Cottage vacation rentals in Middlesex County

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Popular amenities for Middlesex County cottage rentals

Cottage rentals with a hot tub

Superhost
A spacious yard features a hammock suspended between two trees, overlooking the bay. Colorful Adirondack chairs are positioned nearby, creating an inviting spot for relaxation. The calm water stretches into the distance under a clear sky, providing a serene atmosphere.
Cottage in Reedville
4.88 out of 5 average rating, 209 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

LorenRating, 5 stars1 week ago
We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.
Guest favorite
An aerial view captures the spacious backyard featuring a rectangular swimming pool surrounded by a concrete deck. Lounge chairs are placed by the poolside, with a well-maintained lawn and shrubs in the background. The two-story cottage is shown with a screened porch and a shaded area nearby.
Cottage in Chesapeake
4.95 out of 5 average rating, 132 reviews

The Cottage @ Captain Genes - Secluded Waterfront

LindseyRating, 5 stars6 months ago
Our stay in this home was such a treat! We enjoyed utilizing the kayaks to boat around in Chesapeake Bay. The hot tub was an absolute delight, perfect for evening stargazing, saw lots of shooting stars, and could see the water of the bay from the hot tub. We also enjoyed doing November cold plunges from the hot tub to the pool. While the living room is not expansive, it fit our needs for family game & movie nights. The bed linens were so comfortable, and Lori was beautifully responsive & friendly when we would reach out with a question. We also enjoyed the nearby Sandy beaches.
Guest favorite
A hot tub is positioned on a wooden deck, overlooking the shimmering waters of the Chesapeake Bay. Surrounding greenery includes tall grasses and trees, with the expansive view of the water framed by a clear blue sky.
Cottage in Reedville
4.9 out of 5 average rating, 205 reviews

Bay cottage 🏖on the beach. Stunning views🏝

PaulRating, 5 stars1 week ago
We LOVED our stay! The screened porch overlooking the beach was so peaceful and our favorite place to be in the evening. The house was lovely, well cared for, very clean, and very tastefully decorated. The welcome book provided everything you needed to know about the house and surrounding area. We will be back again!
Guest favorite
An outdoor patio area is shown, featuring multiple white chairs arranged in a circle around a stone fire pit. Lush green grass surrounds the space, with potted plants offering touches of color. The scenic view of the river is visible beyond the trees.
Cottage in Gloucester
4.95 out of 5 average rating, 20 reviews

Waterfront Gloucester Cottage w/ Private Boat Dock

RebeccaRating, 5 stars2 weeks ago
We had a great time staying here! Clean, modern, fully stocked home just as described in the listing and photos. The sunsets over the water are indescribable. Relaxing hot tub, wonderful outdoor space, lovely campfires, and comfortable bed and bath rooms made our trip stress free and extremely enjoyable. We barely left the property - we felt right at home. Our point of contact host, Ana, was very responsive and communicative. Would definitely recommend! Look forward to booking again in the future! Thank you for a vibey holiday weekend!
A spacious outdoor area is highlighted by a hot tub surrounded by greenery. A pink umbrella provides shade over a seating arrangement, with flowers in decorative pots enhancing the tranquil setting. A wide lawn extends into the background, offering an open view.
Cottage in Cape Charles

Bungalow w/ Large Yard: 8 Mi to Cape Charles Beach

KierstinRating, 5 stars1 month ago
We absolutely loved staying here! It was the perfect distance from Cape Charles where we visited during the day. It was the perfect little getaway!
Guest favorite
A bright and airy living area features large windows providing views of the surrounding landscape. Comfortable seating is arranged around a circular coffee table on a patterned area rug, while built-in shelves display decorative items. Ceiling fan and light tones enhance the space's openness.
Cottage in Heathsville
4.89 out of 5 average rating, 35 reviews

Waterfront Heathsville Cottage w/ Dock & Hot Tub!

JameseRating, 5 stars2 months ago
This is a really nice getaway that is peaceful and serene. The home is older, but has some nice updates. I am one that appreciates a home with character. It is in a secluded area, so at night its gets really dark in the hot tub area which we made good use of. Waking up to views of the lake was my favorite part of the day. I was sad when the sun started to go down. There are neighbors, but the houses aren't very close to each other. It is located in a small town so there aren't many food options. The restaurant we went to wasn't very good, so I'd highly recommend cooking for your stay or bringing food. That's what we did. We cooked our meals and grilled. It was fantastic. Four of us stayed there comfortably. Two couples. Overall we had a nice 3 days and I'd highly recommend.
Superhost
A serene waterfront view showcases a charming log cabin surrounded by lush greenery. A private dock with several kayaks awaits on calm waters, inviting outdoor activities. The landscape includes tall trees and a peaceful atmosphere, ideal for relaxation by the bay.
Cottage in Foster
4.85 out of 5 average rating, 71 reviews

Old Log Cabin School House w/10 acres on the Bay

MichelleRating, 5 stars5 days ago
Great peace of history in a peaceful location. Kids thought it was coolest place ever to go kayaking, fishing, catching crabs, and relaxing inside playing chess and listening to some records. Richard was very accommodating with how far we had to travel and was able to help with a flexible check in time.
Top guest favorite
A spacious living room features large windows providing ample natural light and views of the surrounding landscape. A cozy sectional sofa is positioned nearby a wood stove. A streamlined table with decorative elements sits in the foreground, while dining chairs are visible in the background.
Cottage in Onemo
5 out of 5 average rating, 46 reviews

3 BR Bay Home w Private Dock & all the Amenities

ChrisRating, 5 stars1 month ago
Our trip to The Half Shell Haven was great! The place was clean, extremely well stocked, and included many extras! We had crazy weather the first two days, but we had plenty to do at the house. My boys loved being on the water and the game room and my daughter loved the hot tub and bicycling. My daughters service dog enjoyed a nice reprieve and seemed so happy. We had a great time, and were honestly sad to go! If we find ourselves back up in Virginia we will definitely stay here! Thank you for the care and attention to detail to ensure a great trip!

Pet-friendly cottage rentals

Guest favorite
An inviting living space features a light-colored sofa and two accent chairs in contrasting hues. A wooden coffee table sits in the center, with natural light flowing through large windows, highlighting the rustic ceiling beams and modern artwork on the wall.
Cottage in Melfa
5 out of 5 average rating, 15 reviews

Whitsapenny Cottage at Vaux Hall Farm

WalterRating, 5 stars2 weeks ago
Would return and recommend to others. Beautiful pristine space with numerous areas for guest to spread out and experience the beauty of the area and learn about the history and renovation of that particular farm and community. Very interesting restoration of existing structures and addition of many more places and ways to learn about and enjoy the natural surroundings.
Superhost
A remodeled cottage is set amidst a green lawn, featuring a spacious screened front porch and surrounded by trees. The building showcases a classic design with a dark exterior and a contrasting light roof, under a clear blue sky.
Cottage in Warsaw
4.93 out of 5 average rating, 119 reviews

Modern 2 Bdrm Cottage in Historic River Community

SherriRating, 5 stars3 weeks ago
Perfect getaway for rest, relaxation and fun! Kayaks were fun, too breezy and chilly waters for paddle boarding, maybe next time! Beautiful location! Clean and comfortable, felt like home!
Top guest favorite
A charming cottage is set against a backdrop of tall trees, showcasing a light-colored exterior. A welcoming front porch features comfortable seating and an American flag. The landscaped yard includes potted plants and a gravel pathway leading to the entrance.
Cottage in Gloucester
4.97 out of 5 average rating, 233 reviews

"Bee Haven" Cottage Retreat

HeidiRating, 5 stars1 week ago
I had a great stay! The space was quiet, and very clean—perfect for relaxing. It was also pet-friendly, which was a big plus. The host was friendly and communicative, making everything easy from check-in to check-out. Would definitely stay again!
Guest favorite
A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.
Cottage in Onancock
4.96 out of 5 average rating, 161 reviews

A "True" Chesapeake Bay Waterfront Experience!

JenniferRating, 5 stars1 month ago
I truly wish I could put into words just how beautiful and peaceful this home and property were. It is truly a place that was so inviting and well maintained it made me miss the eastern shore of Virginia and start looking at properties in the area. The land is so cool to walk and explore and the bay at this home is just serene. To be able to wake up and see the view this home has is just spectacular. Matt is spot on with the description of his home and you truly can't find one thing wrong with this home or the property surrounding it and having a dog,it is so key with the wash station outside because our lab puppy could not get enough of the bay or going out in the kayaks with us. I truly wish they had more stars to rate this home. Thank you for being so gracious and allowing us to visit your spectacular home!
Superhost
A serene sunset is captured over calm waters, with hues of orange and gold reflecting on the surface. Silhouettes of trees frame the scene, while a dock extends into the bay, creating a tranquil coastal atmosphere.
Cottage in Painter
4.89 out of 5 average rating, 93 reviews

Cottage by the bay (private peaceful surroundings)

JorgeRating, 5 stars5 days ago
Very secluded but I don't mind that all. The home is beautiful and the host is very attentive.
Guest favorite
A welcoming porch is featured, lined with wicker chairs adorned with colorful cushions. Potted flowers add a touch of nature, while the sunlight casts gentle shadows across the wooden flooring, creating an inviting atmosphere for relaxation.
Cottage in Gwynn
4.86 out of 5 average rating, 36 reviews

Sunset Haven

ConnieRating, 5 stars7 months ago
This is our second time staying at Sunset Haven— appropriately named. Gorgeous sunsets and weather was perfect. Great and considerate communication with Terri. House was pristine and had every thing you could need. We will be back! Thank you Terri!
Top guest favorite
A red kayak rests at the edge of the serene reservoir, surrounded by trees that frame the waterway. The calm surface reflects the clear blue sky and soft ripples created by a gentle breeze, ensuring a tranquil outdoor experience.
Cottage in Lanexa
4.97 out of 5 average rating, 123 reviews

TooFine Lakehouse, pet friendly waterfront cottage

JenniferRating, 5 stars3 weeks ago
We had a wonderful time! The atmosphere was incredibly peaceful and relaxing—perfect for unwinding, even on the rainy days we had. The space was beautiful, cozy and calm. Gina was a great host—very responsive and proactive in checking in to make sure everything was going well.
Guest favorite
A historic sign for Glebefield, established in 1795, is positioned among mature trees. Bright yellow flowers add a pop of color in the foreground, contrasting with the earthy tones of the surrounding greenery, creating a serene and inviting atmosphere.
Cottage in Gloucester Courthouse
4.98 out of 5 average rating, 213 reviews

Historic Ware River Cottage at Glebefield

KristinRating, 5 stars1 month ago
Incredible stay on a beautiful property. It’s quiet, private, VERY well maintained and just awesome. I truly hope to stay at this location again in the future because it was that great! You can tell the history in the cottage yet it’s updated and cozy. Also I’ve NEVER stayed at a location so clean!!!! From the cottage itself to the grounds, everything was very well taken care of.

Private cottage rentals

Top guest favorite
The living area showcases a mix of wood and painted walls, highlighted by a stone fireplace. Comfortable seating is arranged around a coffee table, while a bar area with stools is present. Large windows invite natural light, enhancing the cozy atmosphere.
Cottage in Weems
4.99 out of 5 average rating, 114 reviews

The Crab Shack

TarynRating, 5 stars2 days ago
This was our 1st visit to The Crab Shack. All I can say is Wow, just Wow! This was the cleanest, nicest and cutest Airbnb that we have ever stayed at over the years! It was amazing! My husband and I traveled from Sarver, PA with our 2 Golden Retrievers to celebrate our 10 year Wedding Anniversary! We all had the best time ever! We spent most of the time here at the Shack just cooking on the grill and listening to music and the girls did a lot of swimming fetching for balls! Thank you Carlisle and Mary for making our 10 year Anniversary simply perfect! ❤️☀️😎🥂🍾🦀 We can’t wait to come back! ☺️
Superhost
A serene view of the water is depicted, featuring soft pastel colors of the sky as the sun sets. Grassy land leads to the edge of the cove, while a kayak and a paddle board are positioned on the ground, ready for use.
Cottage in White Stone
4.89 out of 5 average rating, 353 reviews

The Moore Cottage

LauraRating, 5 stars2 weeks ago
Great spot. Brought a camp chair and binoculars and sat by the shoreline. Drove to the windmill point tiki bar on fleets island for a sunset walk. Enjoyed kilmarnock & white stone. Had a soft shell crab sandwich at Bay Bistro, oysters & crab dip at Tides Inn. Great thrift stores in kilmarnock. Nights were peaceful and starry with the sounds of frogs. Definitely recommend staying here if you’re looking to explore the northern neck.
Top guest favorite
An inviting interior showcases a rustic wooden table surrounded by dark chairs. A basket with supplies rests at the center. The spacious living area features a cozy couch arranged near large windows, creating a bright atmosphere enhanced by wooden beams overhead.
Cottage in Topping
5 out of 5 average rating, 32 reviews

Locklies Innlet, A unique waterfront experience!

LisaRating, 5 stars1 month ago
What a perfect cottage! Beautifully (but comfortably) furnished, right on the water, incredibly well-stocked. Arranged so families can spread out, or gather together. Everything you could possibly require or desire for a vacation or getaway was there. And the area is full of things to do--walks, birdwatching, antiquing, or, if you're an architecture geek like me, historic sites and buildings. You're also a 3-minute walk from the best restaurant on the Northern Neck, Merroir Tasting Room. Can't wait to come back.
Guest favorite
A bright bathroom is showcased with a window that allows natural light to illuminate the space. The walls feature a patterned wallpaper with fish and seashell designs. A white shower curtain hangs beside a clean sink and toilet, offering an inviting and organized atmosphere.
Cottage in Deltaville
4.83 out of 5 average rating, 180 reviews

The Little House at Waveland

AshleyRating, 5 stars3 days ago
We had a great time at Diana’s place. The water access was awesome and we had lots of fun with the kayaks. We were able to walk through a wooded trail to a nearby restaurant which was so nice. The location felt private and naturally beautiful while being not far from grocery stores and restaurants. Diana’s neighborhood is beautiful and the space is charming and comfortable. Such a fun way to see the Chesapeake, we would love to come back!
Top guest favorite
The Gothic Revival-style cottage is showcased from its charming exterior, featuring large arched windows and a welcoming front porch. Two wooden chairs sit invitingly on the porch, complemented by seasonal decorations. Surrounding trees provide a sense of tranquility within the peaceful setting.
Cottage in Irvington
5 out of 5 average rating, 201 reviews

Peaceful Haven: nature & charming town

StephanieRating, 5 stars3 weeks ago
What a wonderful place and host! Pictures do not do it justice. It looks like a cosy cottage on the outside, but it is much bigger on the inside. Very clean. The first floor provides an extremely functional living space - living room, dinning area, kitchen and sun room. The couch in the sun room is extremely comfortable. The bedroom and bathroom upstairs are palatial. The two bedrooms downstairs are very cosy and have their own beautiful bathrooms. One of the downstairs bedrooms has a wonderfully enclosed porch off of it. Everything is up to date and very functional - Wi-Fi, heating and air conditioning, washer & drier, kitchen appliances, etc. And the host was quick to respond to any questions. We hope to return soon and take advantage of the outdoor activities.
Top guest favorite
A wooden boardwalk leads to the sandy beach, flanked by green vegetation. Colorful adirondack chairs in red and blue are positioned on the boardwalk, providing a relaxing view of the surrounding landscape and nearby cottage.
Cottage in Urbanna
4.99 out of 5 average rating, 170 reviews

Little Dipper -private beach,Kayaks & paddleboards

SarahRating, 5 stars6 days ago
Review This was our second time staying in this adorable cottage. We spent 10 days in 2023 & we just spent another 10 days! (May/June 2025) We would love to return again in the future! Clean and cute with a small private beach and gorgeous sunrises! The screen porch and outside shower were a plus! The bed was very comfortable. The kitchen had everything we needed to cook our meals. Kayaking was fun! We brought our bikes and daily biked around the area and we also walked the charming town of Urbanna. We attended church at the Urbanna Baptist Church and met several of the locals who were so friendly and welcoming. What a relaxing delightful place! It was a pleasure meeting Ned on our first day. We cannot say enough good things about this enchanting place. Thank you Ned and Holly for sharing your cottage with us and for the great communication! We hope to visit again!
Guest favorite
Cottage in Kilmarnock
4.95 out of 5 average rating, 41 reviews

Restful river house with water & golf-course view

JimRating, 5 stars2 weeks ago
Kitchen was well stocked. Bathrooms, kitchen, everything was clean, beds were very comfortable. Beautiful yard and sunroom where we spent most of our time. Close to excellent restaurants. We really enjoyed our stay and plan on staying again in the future.
Top guest favorite
An aerial view presents the coastline of Gwynn’s Island, showcasing sandy beaches and calm waters. The Mystic Seahorse and Starlight Inlet cottages are highlighted among the tree-lined landscape. Several boat docks extend into the water, indicating access for recreation and relaxation.
Cottage in Gwynn
4.96 out of 5 average rating, 212 reviews

Mystic Seahorse Cottage & game room

MargieRating, 5 stars2 weeks ago
Mystic Is a quaint, clean and welcoming houae. All details from pictures to knick knacks create a complete theme. Instructions were easy and thoughtful. Communications were prompt and thorough. This home and its owners create a perfect sanctuary.

Destinations to explore