Home Vacation Rentals By Owner In Gloucester, VA

Showing 20 Of 32 Vacation Rentals
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Exceptional(12)

$473.92

/ Nightly
Cottage

Waterfront Gloucester Cottage w/ Private Boat Dock

Gloucester, Virginia, United States

Experience the beauty of Gloucester when you stay at this 3-bed, 2-bath vacation rental. Overlooking the York River, this cottage offers a sunroom, an outdoor dining area, and a fire pit for enjoying chilly evenings, making it the ideal spot for a family or group getaway. If you'd like to venture out, visit Machicomoco State Park!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTS: br- Bedroom 1: King Bed br- Bedroom 2: Queen Bed br- Bedroom 3: Queen Bed br- Sunroom: Queen Sleeper Sofa brbrOUTDOOR LIVING: br- Expanded patiobr- Outdoor cooking area w/ Weber gas grill & 2 dining tables br- Fire pitbr- Private boat dockbr- Spacious yard br- Sunset views br- Outdoor TVbrbrINDOOR LIVING: br- Sunroombr- Smart TVbr- Dining tablebrbrKITCHEN: br- All major appliances, including dishwasherbr- Cooking utensils, dishware/flatwarebr- Coffee maker, microwave, Crockpot, toaster, water purifierbrbrGENERAL: br- Free WiFibr- Central air conditioning br- Complimentary toiletriesbr- Washer/dryer, linens/towelsbr- Trash bags/paper towelsbr- Keyless entrybrbrFAQbr- Quiet hours (11:00 PM-9:00 AM)brbrACCESSIBILITY: br- Single-story home, step-free entrybr- 1 small step in home from hallway to dining room (3-inch drop), stairs to access dock area brbrFAQbr- Interior smoke/excessive noise monitorbr- 1 exterior security camera (facing out)brbrPARKING: br- Driveway (4 vehicles)brbr-- THE LOCATION --brbr- 8 miles to Machicomoco State Parkbr- 13 miles to Gloucester Point Beach Park br- 16 miles to Yorktown Fishing Pier br- 25 miles to Busch Gardens Williamsburg br- 23 miles to Newport News/Williamsburg International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Because there is no fence between the property and the river, the property might not be suitable for young children; adult supervision is recommendedbr- NOTE: This single-story cottage offers step-free entry, but there is 1 minor step (3-inch drop) from the hallway to the dining room. Stairs are required to access the private dockbr- NOTE: This property includes an internal smart device used to measure smoke and excessive noise in the home. It does not have a camera but does measure smoke and volume levels throughout the home while guests are presentbr- NOTE: Your safety matters. This property features 1 exterior security camera located at the front door facing the front entryway. The camera is outward facing and does not look into any interior spaces. The camera records audio at all timesbr- NOTE: Please observe quiet hours from 11:00 PM to 9:00 AM
Bed 3

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Bath 2

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Sleep 6

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Exceptional(5)

$279.08

/ Nightly
Apartment

Family-Friendly Main St Gloucester Apt w/ Balcony!

Gloucester, Virginia, United States

Above Operating Bakery | Quaint Setting | Shared Patio | Great for Traveling Nurses!brbrThis aptly named vacation rental, 'Eden,' is a slice of paradise! The 2-bedroom, 1-bath apartment sits directly on Main Street, and the cherry on top is that it's above the Sweet Tooth Café. Start your morning with a visit to the bakery and plan your day on the patio. History buffs will love the museums, and Busch Gardens is perfect for the whole family. Come home each day to unwind in front of the fireplace.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 bunk bed (twin/full futon)br- Living Room: 1 queen sleeper sofabr- Additional Sleeping: 1 portable cribbrbrINDOOR LIVINGbr- 3 Smart TVs w/ cablebr- Electric fireplacebr- Dining tablebrbrOUTDOOR LIVINGbr- Private balconybr- Outdoor speakersbr- Shared café patio, gas heater & gazebobrbrKITCHEN br- Stove/oven, refrigeratorbr- Dishware/flatware, cooking basicsbr- Dual drip & single-serve coffee makerbr- Microwave, blender, Crockpot, rice cooker, toasterbr- Trash bags & paper towelsbrbrGENERAL br- Free WiFibr- Central A/C & heating, ceiling fansbr- Washer/dryer & laundry detergentbr- Linens/towels & hair dryerbrbrFAQbr- Pet fee (paid pre-trip)br- Sweet Tooth Cafe on-site (attached, located below)brbrACCESSIBILITYbr- Single-story apartment on upper floor, steps to enterbrbrPARKINGbr- Free street parking (first-come, first-served)brbr-- THE LOCATION --brbr- Directly on Main Street above a café near shops & eateriesbr- Walk to Gloucester Museum of Historybr- 25-28 miles to Saunders, Busch Gardens Williamsburg & Colonial Williamsburgbr- 58 miles to Richmondbr- 63 miles to Virginia Beachbr- 24 miles to Newport News/Williamsburg Int'l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $200 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story apartment on the upper floor requires stairs to enterbr- The homeowner operates the lower-level café on-site. The owner and café patrons may be present during your stay
Bed 2

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Bath 1

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Sleep 7

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Exceptional(25)

$385.32

/ Nightly
Private Vacation Home

Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock

Gloucester, Virginia, United States

Welcome to York Overlook! Enjoy this three bedrooms house for the entire family! Put the kids in the bunk room with a single over double bunk bed and a double bed, the kids will enjoy the primary bathroom complete with a shower and separate soaking tub to splash in. There is a second bedroom on the main floor furnished with a single over double bunk bed, great for kids or adults to enjoy. There is a hall bathroom with laundry room and shower also. Upstairs is the primary bedroom that is a true RETREAT with a king bed, separate sitting area, full bathroom and even a lovely balcony to enjoy. The house includes great spaces for recreation for all! the main living area is a fantastic OPEN CONCEPT space including a wonderful updated modern kitchen including breakfast bar seating. There is a cozy kitchen table and a large dining table along with comfortable seating to watch tv and movies. Enjoy AMAZING VIEWS from the full wall of windows. Outdoors features a porch overlooking the river and fenced in yard. The home is on a hill overlooking the river. Enjoy a fabulous dock with a launch for kayaks and a slip for your boat. Home is complete with everything needed to enjoy the water, kayaks, and paddles and life vests. Set up a picnic or play with the kids on the sandy beach by the river. There are outdoor games such as volleyball and cornhole, as well as a myriad of indoor entertainment including table shuffleboard, darts, foosball, games and table puzzles. Truly a WATERFRONT paradise for your family to enjoy.brbrFor a money saving vacation, just stay onsite and enjoy your family time. If you want more adventure there are ample activities just a short drive away. brbrColonial Williamsburg 1 HourbrBush Gardens 1 HourbrCompass Family Entertainment Complex 45 MinutesbrSeveral Small Waterman Museums Within an HourbrDowntown Gloucester 10 MinutesbrGloucester Point Fishing Pier 25 MinutesbrHistoric Yorktown and Yorktown Waterfront Beaches 30 MinutesbrFishing Charters NearbybrSailing Charters are out of Yorktown Waterfront Pier or York River Yacht HavenbrbrThere is also a large flat sandy area between the house and river for the kids to pitch tents and of course there is a fire pit.
Bed 3

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Bath 3

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Sleep 10

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Exceptional(58)

$217.04

/ Nightly
Private Vacation Home

Welcome to The Happy Soul

Gloucester, Virginia, United States

When I think of this house, I think of the quote Let all that you do be done in LOVE. It has truly been a labor of LOVE restoring The Doll House. We are premier host and are excited to add this to our list of rental homes. We have completely transformed this 1940's Bungalow into a place for you to rest & restore your soul. This luxurious and upscale home will not disappoint you with all the modern conveniences needed while exploring our area. Gloucester Courthouse was built in 1766 and is one of the oldest Courthouses still in use today. Hike or rent a boat at Beaverdam Park, sip chardonnay at a nearby winery, dine at one of Gloucester's fine eateries, shop in specialty boutiques and gourmet food shops, visit antique stores, local beaches, buy fresh local seafood & produce from our farmers market and many other attractions sure to keep your vacation memorable for many years. The open floor plan lends itself to easy entertaining and the deck plus a stamped concrete patio is sure to be the families favorite spot for meals or morning coffee. All bedrooms have high end memory foam mattresses. Furnished with care and attention to detail, this home will encourage relaxation and fun. Gloucester Courthouse is 5 miles, Yorktown 20miles, Colonial Williamsburg, Bush Gardens & Water Country 35miles from the property. PLEASE NOTE: We do not rent to anyone under the age of 25. We also do not allow pets or smoking in the home at anytime. We live close by if you need anything at all!
Bed 3

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Bath 2

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Sleep 6

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Exceptional(31)

$196.16

/ Nightly
Private Vacation Home

Radiant Gloucester House w/ Private Porch!

Gloucester, Virginia, United States

Enjoy your next Virginia getaway at this newly renovated 1920s Gloucester vacation rental in the heart of downtown. This 2-bedroom, 1-bathroom home is the perfect home base for anyone in your family, whether they’re history buffs or outdoor enthusiasts! Colonial Williamsburg, Busch Gardens, and Gloucester Point Beach are just a day trip away. Fun local events like the Daffodil Festival are walkable from the front door of the property, as well as shops, dining, and breweries.brbr-- THE PROPERTY --brbrPet Friendly w/ Fee | Sunroom | Piano | Great Main Street Location brbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Office: Twin Daybed w/ TrundlebrbrOUTDOOR LIVING: Patio furniture, outdoor dining brINDOOR LIVING: Dining table, shower/tub combo, ceiling fans, books, fireplace (decorative)brKITCHEN: Refrigerator, coffee maker, stove/oven, microwave, dishwasher, toaster, blender, dishware & flatware, cooking basicsbrGENERAL: Free WiFi, keyless entry, self check-in, central heating & A/C, washer & dryer, iron/board, towels/linens, trash bags/paper towels, hair dryerbrFAQ: Pet fee (paid pre-trip), 3 steps required for accessbrPARKING: Driveway (2 vehicles), free street parking, RV/Trailer parking allowed on-sitebrbr-- THE LOCATION --brbrOUTDOORS: Beaverdam Park (3 miles), Warehouse Boat Ramp (3 miles), Williams Wharf Landing (19 miles), New Point Comfort Lighthouse (26 miles)brHISTORIC SITES: Gloucester Museum of History (0.3 miles), Fort Nonsense (10 miles), Yorktown (14 miles), Williamsburg (28 miles), Jamestown (35 miles)brLOCAL ATTRACTIONS: Shoppes At Gloucester (2 miles), Zoll Vineyards (10 miles), The Dog and Oyster Vineyard (26 miles), Busch Gardens Williamsburg (27 miles), Silver Hand Meadery (28 miles), Great Wolf Lodge Water Park (33 miles), Downtown Hampton (34 miles)brAIRPORT: Newport News/Williamsburg International Airport (23 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $100 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires 3 steps to accessbr- NOTE: The fireplace is decorative only and not for guest use
Bed 2

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Bath 1

Bath

Sleep 6

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$143.17

/ Nightly
Private Vacation Home

Bee Haven Cottage Retreat Near Colonial Williamsburg

Gloucester, Virginia, United States

Curious about what makes Gloucester so wonderful Live like a local at Bee Haven Cottage Retreat and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious open floor plan living area allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee or come out to the inviting front porch to listen to the birds chirping or star gazing while sipping evening wine. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.brbrLIVING ROOM:br *Smart 55 TV, Cable Wifi Wireless Internet throughout entire housebr *Lounge Couch comfortable for 4 & Side Chairbr *Board Games, Uno & deck of cardsbr *Plenty of lightingbr *Ceiling fan & throw blankets for long napsbr *Main Entry Door, 3 windows with blinds & curtainsbrbrDINING AREA:br *Table with 4 chairs & 2 bar stoolsbrbrKITCHEN:br *Electric stove/Oven, Microwave, Refrigerator w/ice maker & filtered waterbr *Dishwasher & dishwasher tablets provided, toaster, mixer, blender, can openerbr *Mr. Coffee 12 cup coffee pot & filters (bring your own coffee)br *Keurig Single Serve Coffee Pot (bring your own pods)br *Completely stocked with cooking needs, including a selection of pots, pans, serving br dishes, platters, cookie trays, etc.br *Enough forks/spoons/knives/plates for everyonebr *Includes 1 roll of paper towels, dishwashing soap, a sponge, dish cloths & dish towelsbr *Full size Washing Machine (bring your own detergent)br *Full size Dryer & dryer sheets includedbrbrMASTER BEDROOM:br *Queen size memory foam mattress with warm, comfy quilt, high end sheets, 4 pillows,br mattress protector to ensure a good night sleepbr *2 windows with blinds & black out curtainsbr *2 large closets with plenty of storage space & hangersbr *Ironing board & ironbr *1 reading chair, ceiling fan & lightbr *2 bedside reading lights perfect for night readingbrbrBEDROOM 2:br *Queen size memory foam mattress with warm, comfy quilt, high end sheets, 4 pillows,br mattress protector to ensure a good night sleepbr *2 windows with blinds & black out curtainsbr *Ceiling fan with lightbr *1 bedside lamp perfect for night readersbr *Full size dresser & mirror, closet with hangersbrbrBATHROOM:br *Vanity with marble top, tub & shower combo perfect for long relaxing bathsbr *Tiled oversized shower & tiled entire bathroom floorbr *Shampoo, conditioner, hand & body soap, dryer, towels, wash clothes, hand towels,br & toilet paperbrbrBACK DECK:br *Located off the kitchenbr *Table & chairs for 2br *Outdoor propane grill, complete with tank of propane,br with extra tanks located under back deck, grilling utensilsbrbrFRONT PORCH:br *Wicker loveseat & chairs comfortable seating for 4br *Perfect for morning coffee or evening wine listening to the birds chirping, star gazing & br nature at its bestbr *Outdoor string lighting on a timerbr *Motion sensor light by front doorbr *Glass storm door which glass moves up and down to provide a screen door for fresh air
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Bath 1

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Sleep 4

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Exceptional(114)

$142.36

/ Nightly
Guest House

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Gloucester, Virginia, United States

Welcome to this guesthouse garage apartment on the North River in Gloucester! Lots of special events are going on for the US 250th Anniversary in our region of American Colonial History. Enjoy a quiet retreat at this private setting overlooking both a river and a creek in Gloucester County. The guesthouse is a separate building from the owners' house, and is very private. Nestled in an area of historic estates and down a long country lane, this guest house apartment offers a base for exploring the nearby Historic Triangle – Williamsburg, Jamestown and Yorktown -- the latter where we won the Revolutionary War. Check out the websites of these individual attractions for further information. You can also explore the rural counties of Gloucester and Mathews with historic courthouses and charming shops. While the property feels away-from-it-all, it is only five miles from the village of Gloucester with restaurants, grocery stores, a gourmet shop with prepared foods, and clothes and jewelry and gift shops. It is also a short drive to an historic country store on neighboring Ware Neck that has both prepared foods and a wine shop, and it is near the world-renowned gardens of Brent and Becky's Bulbs. A canoe and two kayaks are available for paddling or fishing. Country walks, birding, or quiet reading on a deck overlooking both a river and a creek are relaxing pastimes that await you. Guests also have access to the owners' private dock and can fish from the dock, the shore or the kayaks. brbrThe apartment contains 1 separate bedroom, a large living room with kitchen and dining nook, 1 bathroom, and a deck overlooking woods and water. The deck can seat 4. The bedroom has a queen bed, and the living room has a couch that turns into a queen size futon bed so the space can accommodate 4 people. Guests say that the property is a great place to chill out for a quiet few days or week, or to use as a base for touring the many historic areas in Tidewater Virginia. Longer term stays are also welcome. There are many cultural activities in Jamestown, Yorktown, and Colonial Williamsburg in addition to the historic sites themselves. The villages of Gloucester and Mathews also have various festivals and events throughout the year, among them the Gloucester Daffodil Festival in late March and the Garden Club of Virginia Historic Garden Week tour in April. This area of Gloucester County was once known as the Venice of Tidewater, and today is still known as the land of life worth living. Internet service is available through a Verizon Jetpack. Come for a visit to beautiful Tidewater Virginia!
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Bath 1

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Sleep 4

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$333.9

/ Nightly
Cottage

Mid-Century Rivah Retreat with Dock, Fire Pit & Cozy Fireplace

Gloucester, Virginia, United States

Nestled along the Piankatank River in Gloucester, this charming cottage is an invitation to slow down, breathe deeply, and reconnect—with nature, with the people you’re traveling with, and with a simpler rhythm of life. From the moment you arrive, the river views, quiet surroundings, and cozy character of the home set the tone for a true retreat.brbrInside, the house is warm, comfortable, and thoughtfully set up for real living. There are two cozy bedrooms designed for great sleep after days spent outdoors: one with a luxurious king bed, another with a full bed and a twin—perfect for couples, friends, or families. The bathroom features a refreshing shower and a hair dryer, and the home includes air conditioning, heat, WiFi, and a fireplace to make it comfortable year-round. The living space is welcoming and relaxed, ideal for reading, playing games, or simply enjoying the view as the light changes over the river.brbrOutside is where this home truly shines. A deep-water dock offers direct access to the river and plenty of space to linger. Dock chairs invite you to sit with your morning coffee, watch the osprey and boats drift by, or enjoy a quiet sunset at the end of the day. In the evenings, gather around the fire pit—one of our favorite spots—for conversation, stargazing, and winding down as the fire crackles. It’s the kind of place where phones naturally get set aside and time stretches a little longer.brbrThe home is also very family-friendly. We provide a Pack ’n Play and a high chair, along with space for kids to play and explore, making it easy to travel lightly and settle in comfortably.brbrWhile the property feels tucked away and peaceful, you’re still close to everything you might need. Grocery stores and local essentials are about 15 minutes away, as is a nearby brewery. Merrior is just 20 minutes away for oysters and waterfront dining, and you’re about 30 minutes from The Tides Inn and the charming towns of White Stone. One of our favorite local spots, Adrift, is also an easy drive and well worth the visit.brbrWhether you’re coming for a weekend, a week, or a longer stay, this cottage is a place to truly decompress—wake up with the river, spend your days outside, and fall asleep to quiet nights. It’s a home designed for living simply, resting deeply, and falling in love with rivah life.
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Sleep 5

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Exceptional(25)

$471.19

/ Nightly
Private Vacation Home

Gloucester Retreat w/ Backyard Oasis & Pier!

Gloucester, Virginia, United States

Pack your bags and head to this charming 4-bedroom, 2.5-bathroom vacation rental home nestled next to the York River in Gloucester. Boasting a stunning backyard space with river views, outdoor dining areas, a private fishing pier, ample entertainment space, and much more, this ideally located abode will have you and your family feeling right at home. Spend days relaxing at the home’s private beach area, perusing the American Revolution Museum at Yorktown, or visiting Busch Gardens Williamsburg.brbr-- THE PROPERTY --brbrRiver Access | 2,400 Sq Ft | Washer/DryerbrbrIdeal for a stress-free family retreat or a fun-filled getaway with close friends, this well-appointed home offers guests easy access to the river and the area’s top attractions without sacrificing the comforts of home.brbrBedroom 1: King Bed | Bedroom 2: Full Bed | Bedroom 3: 2 Twin Bunk Beds | Bedroom 4: Twin Bunk Bed, King Bed (2 Twin Beds Pushed Together)brbrINDOOR LIVING: Smart TVs, fireplace, ceiling fans, dining table, laptop workspace, sewing machinebrKITCHEN: Fully equipped, Keurig coffee maker, cooking utensils, dishware & flatware, hot water pot, microwave, island w/ seating, wine refrigerator, toaster ovenbrOUTDOOR LIVING: Private beach area, patio w/ seating, dining area, gas grill, river views & access, fire pit, private pier, kayak, canoe, & standup paddleboard w/ life vestsbrGENERAL: Free WiFi, lockbox entry, central air conditioning, complimentary toiletries, hair dryers, hangers, in-unit laundry machines, laundry detergent, iron/board, linens/towels, trash bags/paper towels, telescopebrFAQ: Steps required, no fence before riverbrPARKING: Driveway (6 vehicles)brbr-- THE LOCATION --brbrNEAR THE WATER: York River (on-site), Cappahosic Public Beach (0.3 miles), Tanyard Boat Ramp (7.3 miles), Beaverdam Park (10.0 miles), Warehouse Boat Ramp (10.4 miles), Machicomoco State Park (10.9 miles), Gloucester Point Beach Park (16.3 miles), Williamsburg Charter Sails (16.4 miles), Yorktown Sailing Charters (17.5 miles), Yorktown Beach (17.6 miles), Yorktown Fishing Pier (18.6 miles)brTHINGS TO DO & SEE: Gloucester Museum of History (8.2 miles), American Revolution Museum at Yorktown (17.5 miles), Water Country USA (27 miles), Busch Gardens Williamsburg (29.8 miles), Colonial Williamsburg (29.8 miles), College of William & Mary (30.9 miles), Williamsburg Premium Outlets (35.4 miles), Great Wolf Lodge Williamsburg (35.7 miles), Historic Jamestowne (37.8 miles), Williamsburg Botanical Garden (41.6 miles)brBREWERIES & WINERIES: Gloucester Brewing Company (8.4 miles), That Damn Mary Brewing Company (9.1 miles), Zoll Vineyards (17.3 miles), Anheuser-Busch Inc (28.5 miles), Gauthier Vineyard (28.7 miles), The Virginia Beer Company (29.4 miles), Silver Hand Meadery (31.6 miles), Williamsburg Winery, Ltd. (34.1 miles)brAIRPORT: Newport News/Williamsburg International Airport (26.5 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: This property may not be suitable for young children due to there being no fence between the home and the river. Adult supervision is recommendedbr- NOTE: Garage not available for guest use
Bed 4

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Bath 2

Bath

Sleep 10

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Home Most popular vacation rentals in Gloucester