Pet-friendly holiday rentals in Middlesex County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Middlesex County

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

Home in Irvington

4.99 out of 5 average rating, 111 reviews

The Rosé Retreat: Fireplace-Screened Porch-RELAX

Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

Top Guest favourite

Cottage in Weems

4.99 out of 5 average rating, 106 reviews

The Crab Shack

Enjoy the sunrise at this unique and tranquil getaway! This property was originally a seafood processing facility...hence The Crab Shack! Watch all the action on the water right out the front door with local waterman in and out of beautiful Carter's Creek to and from the Rappahannock River and Chesapeake Bay. There are marinas and The Tides Inn very close by. This property provides privacy and a short 10 minute drive to nearby restaurants and shops in Irvington, Kilmarnock, and White Stone.

Top Guest favourite

Home in Locust Hill

4.97 out of 5 average rating, 127 reviews

Waterfront Cottage Getaway Pool/Kayaks/Fireplace

A timeless cottage on a private, quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront Adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

Guest favourite

Barn in Cobbs Creek

4.95 out of 5 average rating, 112 reviews

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Guest favourite

Home in Grimstead

4.86 out of 5 average rating, 296 reviews

Gwynns Island Waterfront Getaway

Great cottage on the water with a fantastic view of the bay and best sunset on the east coast. Sliding glass doors make it feel like your on the water when your sitting on the couch or in the kitchen. You can crab, fish, kayak, grill out and swim right off the back deck. Very peaceful and relaxing. The newly renovated island restuarant is a mile away with a bar and bascically anything you would want to eat. My father left us the house, we use all the proceeds from Airbnb to make improvements.

Guest favourite

Home in Kilmarnock

4.96 out of 5 average rating, 119 reviews

Belle Haven - High Speed internet, walk to town

Escape to our charming, newly updated cottage, thoughtfully decorated to create a cozy home away from home. Just a 10-minute walk brings you to the heart of Kilmarnock, where you'll find shops and restaurants. A short drive will take you to Irvington and White Stone, where you can explore more dining, shopping, and attractions like The Tides Inn and Compass Entertainment. Nestled in a quiet neighborhood, the cottage offers plenty of privacy, and a fenced yard perfect for your furry companion.

Guest favourite

Tiny home in Deltaville

4.97 out of 5 average rating, 178 reviews

Nan's Place aka Down Easter

This cabin is very Unique. The front portion of the cabin is a wheel house off of an old Steam boat. The twin bed is in this part of the wheel house. This cabin has a great water view with a large deck and a screened in porch. It has a full bath. The main living area is basically a studio with a queen bed, full size fridg, micro, toaster oven, stove, kitchen sink, keurig, charcoal bbg grill. This is a dog friendly (no cats, sorry) cabin and is located in a small campground called Cross Rip.

Top Guest favourite

Home in Deltaville

4.95 out of 5 average rating, 150 reviews

The Oyster House

PETS MUST BE PRE-APPROVED ($45 pet fee)! If a quiet country setting is your relaxation, this is your place. Surrounded by open fields that attract deer, turkey, osprey, ground hogs, this is natures haven. Outdoor seating around a permanent firepit or covered backporch with bar top overlooking wildlife. Renovated 2019. Yet, just seconds from downtown Deltaville. House accommodates wheelchairs. Bonus Event Room (The Spat) for 4 people available for extra cost. Ask re: price/availability.

Top Guest favourite

Home in White Stone

4.99 out of 5 average rating, 100 reviews

1891 Coastal Charmer: fully renovated farmhouse

Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

Top Guest favourite

Guesthouse in Saluda

4.94 out of 5 average rating, 516 reviews

Wooded Cabin retreat on fresh water pond

If your looking for a quiet place in a wooded setting, this is it. Cabin has view of private 7.5 acre pond, deck and walking trail to the scenic Dragon Run, with canoe portage. You are welcome to bring your canoe/kayak. Bird watchers, wildflower enthusiasts will enjoy what the Dragon Run has to offer. If shopping or history is your interest, this cabin is only 45 min away from Williamsburg, and will give you a place to relax. This is a pet friendly cabin.

Top Guest favourite

Cottage in Irvington

4.98 out of 5 average rating, 161 reviews

Charming cottage next to Tides Inn with big yard

•Built in 1875, beautifully renovated •1230 sq. ft. •Level 1: Living +Family Room+Kitchen+1 Bedroom+2 Baths (no tubs) + Porch with daybed •Level 2: 1 Bedroom with daybed and 1/2 bath •Deck with views of Carter's Creek •Backyard: Large with tons of yard games & Solo fire pit •Private driveway •Steps from the Tides Inn •Minutes walk to shops, restaurants, bars in town •Free access to bikes •Small dogs permitted with host approval

Guest favourite

Home in Kilmarnock

4.93 out of 5 average rating, 103 reviews

Waterman's Waypoint

Waterman’s Waypoint is a newly renovated, pet friendly 3 bedroom waterfront home located on Prentice Creek. The perfect serene getaway, the property is 3 miles from the town of Kilmarnock, Virginia. There is a private dock and boat ramp perfect for personal watercraft and a deep water slip to accommodate up to a 60’ yacht. New in 2021, Adirondack Chairs, a new Fire Pit and new mattresses on the twin beds.