Top Cottages in Middlesex County in 2026

Middlesex County Cottages
Virginia
United States of America
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Top Cities in Middlesex County

Urbanna

Our top choices for Middlesex County cottages

A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

A living room with a red patterned rug, a white armchair, a black leather sofa, and a bookshelf filled with books.

A spacious living room with a large bookshelf, a leather armchair, a patterned rug, and a cozy seating area with a red sofa and pillows.

A white wooden house with a gabled roof, a front porch, and a satellite dish.

1. Restored 1930s Cottage on 1 Acre w/ Fire Pit

Restored 1930s Cottage on 1 Acre w/ Fire Pit

Hayes

9.6 out of 10, Exceptional, (95 reviews)

9.6/10

Exceptional

(95 reviews)

"Our family of 6 (age range 20’s to 80’s) enjoyed all of the rooms and porches. The air conditioners kept the home comfortable and the porches were cozy for those who like it warmer. We liked the convenience of being able to make our own breakfasts and dinners here. Having a grill was a bonus."

Susan C.

The price is AED 485

AED 485

AED 1,288 total

includes taxes & fees

15 Oct - 16 Oct

Restored 1930s Cottage on 1 Acre w/ Fire Pit

A wooden deck with a white fence and a lounge chair, overlooking a calm body of water during sunset.

A modern kitchen with stainless steel appliances, a large window, and a view of the ocean.

A room with a view of the sea, a table with a fish-shaped tray, wicker furniture, and a lamp.

A spacious room with a large window overlooking the sea, a ceiling fan, and a dining area with chairs and a table.

2. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset

Cape Charles

9.4 out of 10, Exceptional, (24 reviews)

9.4/10

Exceptional

(24 reviews)

"Gorgeous property and excellent host!"

Ryan M.

The price is AED 579

AED 579

AED 1,629 total

includes taxes & fees

14 Oct - 15 Oct

Smith Beach cottage w/ private sunset

A modern house with a covered porch, a large tree, and a kayak in the background.

A spacious living room with a beige sofa, a round coffee table, and striped armchairs. There is a dining area with a white table and chairs.

A dining area with a wooden table, white chairs, a vase with greenery, and a view of the outdoors through large windows.

A calm beach with wooden piers and a boat docked at one end.

3. The Little Blue Cottage - Topping : Waterfront!

The Little Blue Cottage - Topping : Waterfront!

Topping

9.8 out of 10, Exceptional, (61 reviews)

9.8/10

Exceptional

(61 reviews)

"We spent four days in the cottage and enjoyed every minute. Very clean with super comfortable beds not to mention the beautiful view from the master bedroom and the living room..peaceful location with a quick walk to the marina. The host has a book of recommended restaurants nearby and we highly recommend the Local for coffee and breakfast. I will definitely stay in this cottage again."

Agnieszka A.

The Little Blue Cottage - Topping : Waterfront!

A white house with a porch, surrounded by trees and a gravel path.

A white gazebo with a brick roof, surrounded by a white picket fence and lush greenery.

A white picket fence with pink flowers in the foreground.

A cozy room with a fireplace, a bench, a table with a lamp, and a window with blinds.

4. Historic Cottage on Ware River Estate

Historic Cottage on Ware River Estate

Gloucester

10.0 out of 10, Exceptional, (293 reviews)

10/10

Exceptional

(293 reviews)

"Enjoyed our stay - loved the historical setting! "

Bill P.

Historic Cottage on Ware River Estate

A wooden deck leading to a body of water with a clear sky.

A man kneeling on a sandy beach with footprints, proposing to a woman standing nearby.

A cozy interior with a large window overlooking a body of water, a sofa, a small table, and a lamp.

A room with a view of a body of water, a table with a lamp, and a chair.

5. Waterfront Cottage w Private Beach on Chesapeake Bay!

Waterfront Cottage w Private Beach on Chesapeake Bay!

Grimstead

10.0 out of 10, Exceptional, (234 reviews)

10/10

Exceptional

(234 reviews)

"Wonderful rental property. Gorgeous views of the bay! Kitchen is well-equipped with everything you need. Area is peaceful and quiet. We loved the private beach area and the mornings were shady. Would stay here again!"

Sharon S.

Waterfront Cottage w Private Beach on Chesapeake Bay!

A covered outdoor area with a hot tub, seating, and a view of a lake.

A spacious kitchen with a central island, a dining area with wooden chairs, and large windows providing views of the outdoors.

A modern kitchen with white cabinetry, a stainless steel refrigerator, and a granite countertop.

A spacious bedroom with a large bed, a ceiling fan, and multiple windows offering a view of trees.

6. Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

Gloucester

10.0 out of 10, Exceptional, (199 reviews)

10/10

Exceptional

(199 reviews)

"Beautiful location and home! Our days were spent walking up every morning drinking coffee overlooking the bay, relaxing at night in the hot tub, fishing off the pier, and kayaking. One of the best places we have ever rented. Absolute dream for a summer vacation for my husband and I!"

Breanna D.

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

A wooden deck leading to a beach with a sunset in the background.

A cozy living room with a sofa, a coffee table, and a lamp. There is a sliding glass door leading to another room with a dresser and a chair.

A beach with clear water and a sandy shore.

A house with a porch, a wooden fence, and a view of the sea.

7. BEACH COTTAGE BY THE SEA....

BEACH COTTAGE BY THE SEA....

Reedville

9.8 out of 10, Exceptional, (41 reviews)

9.8/10

Exceptional

(41 reviews)

"Very nice place to enjoy a a beach view. The atmosphere is very great!"

Daniel F.

BEACH COTTAGE BY THE SEA....

A wooden deck with two striped beach chairs facing a calm body of water.

A modern bathroom with a glass shower enclosure, a white toilet, a sink, and a shower curtain.

A bedroom with a large bed, a painting of sailboats on the wall, and a window with blinds.

A living room with a fireplace, a dining table with placemats, and a blue vase with flowers.

8. Bubba Butler's Cottage

Bubba Butler's Cottage

Locust Hill

10.0 out of 10, Exceptional, (40 reviews)

10/10

Exceptional

(40 reviews)

"Great cottage with lots of space. Stunning sunrises & sunsets. Thoroughly enjoyed our stay."

Karla H.

Bubba Butler's Cottage

A wooden deck with two green metal chairs and a table, overlooking a body of water.

A room with wooden walls, two beds with floral bedding, a white nightstand with lamps, and a window with blinds.

A house with a wooden porch, a staircase leading to the entrance, and a view of the ocean.

A clear lake with wooden docks extending into the water, surrounded by grassy areas and trees.

9. Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

Heathsville

9.6 out of 10, Exceptional, (131 reviews)

9.6/10

Exceptional

(131 reviews)

"Amazing location. Perfect host. Very quiet location. Special place to visit and relax. Hope to come back again!"

Robin F.

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

A wooden pier leading to a dock, surrounded by calm water.

A dining area with a round wooden table, white walls, and large windows with blinds.

A spacious hallway with wooden flooring, a dining area with a table and chairs, and large windows providing natural light.

A kitchen with white cabinetry, a wooden floor, and a window with blinds.

10. Romantic Waterfront Abode with Patio & Dock!

Romantic Waterfront Abode with Patio & Dock!

Deltaville

9.8 out of 10, Exceptional, (68 reviews)

9.8/10

Exceptional

(68 reviews)

"Great little place on the water. The view was great, the neighborhood was quiet and we had a wonderful weekend to relax. "

Eden A.

Romantic Waterfront Abode with Patio & Dock!

A two-story house with a prominent brick chimney, a front porch with steps, and a small garden with various plants.

A kitchen with white cabinets, a wooden countertop, a ceiling fan, a microwave, and a clock on the wall.

A room with a wooden table, a lamp, a white swan sculpture, and a bookshelf with various decorative items and a sign that reads "ESCAP".

A small house with a fenced yard and a view of the water.

11. Cottage on a Private Island in the York River

Cottage on a Private Island in the York River

Gloucester Point

10.0 out of 10, Exceptional, (383 reviews)

10/10

Exceptional

(383 reviews)

"Most peaceful property I have stayed at. We loved the views, fishing, beach combing, and enjoying family time. Loved this home!"

Alexis P.

Cottage on a Private Island in the York River

A covered patio with a view of the beach, outdoor furniture, and hanging planters.

A bedroom with a brick wall, a bed with a dark brown bedspread, a bedside table with a lamp, and a wall-mounted mirror.

A brightly colored living room with a sofa, a dining table, and a chandelier.

A living room with a brown sofa, teal and white patterned pillows, a glass coffee table with a vase of flowers, and a yellow wall with a mirror and a 'HAPPY' sign.

12. Oceanfront White Stone Cottage w/ Private Beach!

Oceanfront White Stone Cottage w/ Private Beach!

White Stone

7.4 out of 10, Good, (92 reviews)

7.4/10

Good

(92 reviews)

"The house is quirky and fun. The view is incredible and we all felt at peace just hanging out in the backyard, feet from the crashing waves. We will definitely return!"

Lori P.

Oceanfront White Stone Cottage w/ Private Beach!

A house with a porch, a flag, and a view of a lake.

A paved driveway leading to a wooden fence, surrounded by greenery and a small building.

A cozy room with a plaid sofa, a small table, and a view of a lake through large windows.

A bathroom with a shower, a bathtub, and a shelf with toiletries.

13. Waterfront with Private Pier and Tranquil Water views!

Waterfront with Private Pier and Tranquil Water views!

Gloucester Courthouse

10.0 out of 10, Exceptional, (116 reviews)

10/10

Exceptional

(116 reviews)

"great accomodations!"

Mark D.

Waterfront with Private Pier and Tranquil Water views!

A wooden dock leading to a house with a porch and outdoor seating area.

A fireplace with a decorative shell wall, a framed picture above it, and a wooden floor.

A wooden pier leading to a house with a dock.

A bedroom with a large bed, two windows with a view of the sea, a drying rack, and a door leading to another room.

14. The Crab Shack on Carter's Creek

The Crab Shack on Carter's Creek

Weems

10.0 out of 10, Exceptional, (91 reviews)

10/10

Exceptional

(91 reviews)

"This place is a well-hidden paradise! The owner is very responsive. My husband enjoyed paddle boarding and exploring the area. We really enjoyed our stay. "

Karen R.

The Crab Shack on Carter's Creek

A deck with a pool, surrounded by trees.

A modern bathroom with a white vanity, a round mirror, and a glass shower enclosure.

A wooden deck with a pergola, surrounded by trees.

A spacious living room with a sofa, coffee table, and chairs, large windows, and a ceiling fan.

15. Waterfront Urbanna Home w/ Private Dock

Waterfront Urbanna Home w/ Private Dock

Urbanna

9.8 out of 10, Exceptional, (15 reviews)

9.8/10

Exceptional

(15 reviews)

"It was a beautiful home to spend our anniversary. We might come next year."

Lisa Y.

Waterfront Urbanna Home w/ Private Dock

A building with a white picket fence, a dog park sign, and a bench outside.

An aerial view of a lakeside property with a marina, multiple buildings, and a well-maintained lawn.

A waterfront restaurant with tables set for dining, overlooking a calm lake with boats and a building in the background.

A glass-enclosed shower with white tiles and a patterned floor, a towel hanging on a rack, and a window with colorful butterfly decals.

16. Autumn in Virginia where the air is delightful!

Autumn in Virginia where the air is delightful!

Irvington

10.0 out of 10, Exceptional, (319 reviews)

10/10

Exceptional

(319 reviews)

"Quaint home with ideal location. Felt like a second home and would rent again!"

Daryl M.

Autumn in Virginia where the air is delightful!

A coastal property with a grassy lawn, a wooden deck, and a view of the sea.

A living room with a blue sofa, two pillows, a lamp, and a wooden coffee table.

A house with a sloped roof and a visible gutter. There is a grassy yard with a wooden fence and some bushes.

A compact kitchen with white cabinets, a wooden countertop, a sink, and a stove.

17. Relax and Renew on your private deck overlooking the Chesapeake Bay

Relax and Renew on your private deck overlooking the Chesapeake Bay

Silver Beach

9.8 out of 10, Exceptional, (33 reviews)

9.8/10

Exceptional

(33 reviews)

"Quaint beach cottage with amazing bay access and sunsets!"

Teresa Y.

Relax and Renew on your private deck overlooking the Chesapeake Bay

A single-story house with a front porch, a flag, and a well-maintained lawn.

An outdoor seating area with Adirondack chairs and a circular fire pit surrounded by gravel.

A living room with a ceiling fan, a sofa, a coffee table, and a chair.

A dining area with a round table, four chairs, a hanging light fixture, and a window with blinds.

18. Bee Humble Cottage w/in 20mins to Public Beaches

Bee Humble Cottage w/in 20mins to Public Beaches

Gloucester

9.8 out of 10, Exceptional, (37 reviews)

9.8/10

Exceptional

(37 reviews)

"Such a great stay. Would stay again for sure if welcomed back. So peaceful! And clean!"

Josh O.

Bee Humble Cottage w/in 20mins to Public Beaches

A lakeside cabin with a deck and a small shed, surrounded by greenery and a clear sky.

A dining table set with plates, cutlery, and a candle in a room with large windows and a view of trees.

A room with a large window, a desk with a lamp, and a basket on the windowsill.

A dining area with a wooden table set for four, surrounded by chairs. A chandelier hangs above, and a television is mounted on the wall.

19. Golden Days River Cottage - Family & pet friendly, river view, water access

Golden Days River Cottage - Family & pet friendly, river view, water access

Lancaster

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Awesome place, very dog friendly, host is great"

Brian B.

Golden Days River Cottage - Family & pet friendly, river view, water access

A white house with a black front door, a small porch, and a gravel driveway.

A cozy living room with a fireplace, a white sofa, a wooden coffee table with fruit, and a ceiling fan.

A cozy living room with a sofa, a dining table, and a kitchen area with wooden cabinets and a hanging plant.

20. Bay Dream Believer Cottage on Beautiful East River Waterfront

Bay Dream Believer Cottage on Beautiful East River Waterfront

Mathews

10.0 out of 10, Exceptional, (24 reviews)

10/10

Exceptional

(24 reviews)

"Wonderful location, host communicated well"

Nicole K.

Bay Dream Believer Cottage on Beautiful East River Waterfront

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Middlesex County Hotel Reviews

Holiday Inn Club Vacations Williamsburg Resort by IHG

10/10 Excellent

"The staff Deja snd Keara are awesome and professional!! The room was first rate!"

Stephanie 2-night trip

Posted 18 hours ago

Holiday Inn Club Vacations Williamsburg Resort by IHG

Howard Johnson by Wyndham Williamsburg

10/10 Excellent

"Loved the private hot tub. Bed and loveseat were great. My overall experience was superb. My only complaint / wish that something was different was the TV. Wish they were smart tvs with the ability to pull up things like Netflix, Fandango, Amazon etc and log into my account to view them instead of being limited to cox cable."

James 2-night trip

Posted 19 hours ago

Howard Johnson by Wyndham Williamsburg