Cottage holiday rentals in Middlesex County

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Popular amenities for cottage rentals in Middlesex County

Cottage rentals with a hot tub

Superhost
Cottage in Reedville
4.88 out of 5 average rating, 210 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 favourite
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 favourite
Cottage in Reedville
4.9 out of 5 average rating, 205 reviews

Bay cottage 🏖on the beach. Stunning views🏝

PaulRating, 5 stars2 weeks 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 favourite
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!
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 favourite
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
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 stars1 week 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 favourite
Cottage in Onemo
5 out of 5 average rating, 46 reviews

3 BR Bay Home w Private Dock & all the Amenities

ChrisRating, 5 stars2 months 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

Superhost
Cottage in Warsaw
4.93 out of 5 average rating, 120 reviews

Modern 2 Bdrm Cottage in Historic River Community

C. CaliRating, 5 stars2 weeks ago
Loved staying at this quiet retreat! Mornings listening to birds, afternoons in the sunny backyard, stars and stars! Really loved this place and will be back again.
Top guest favourite
Cottage in Gloucester
4.97 out of 5 average rating, 234 reviews

"Bee Haven" Cottage Retreat

KristenRating, 5 starstoday
If you’re on the fence about booking don’t be. Shannons place was absolutely perfect. Set in a quiet neighborhood it was so peaceful! The house was amazing, clean, and comfortable. Shannon went above and beyond to make our stay personal and cozy. Would definitely stay again!
Guest favourite
Cottage in Onancock
4.96 out of 5 average rating, 162 reviews

A "True" Chesapeake Bay Waterfront Experience!

KristenRating, 5 stars3 weeks ago
Second time staying at one of the cottages and can’t wait to come back! The area is so peaceful and serene - great DC getaway. If you enjoy hearing just the bay waves crashing and birds, beautiful sunsets, and panoramic views even from inside look no further.
Superhost
Cottage in Painter
4.89 out of 5 average rating, 94 reviews

Cottage by the bay (private peaceful surroundings)

JamesRating, 5 stars1 week ago
It was a pleasure finding this peaceful home. It is nestled in a rural area of Maryland. If you need to get away from life for a reset, this is the perfect place. The host was extremely responsive and flexible. The home is nicely accommodating and the local area has a nice park and dock to enjoy the water. I would highly recommend staying. James P
Guest favourite
Cottage in Melfa
5 out of 5 average rating, 11 reviews

South Cottage at Vaux Hall w/Roll Up Garage Door

CatherineRating, 5 stars5 months ago
What a truly special place Vaux Hall Farm is! The cottage and location couldn’t be nicer. Thanks to Eric for the warm hospitality too!
Guest favourite
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 favourite
Cottage in Lanexa
4.97 out of 5 average rating, 124 reviews

TooFine Lakehouse, pet friendly waterfront cottage

AlisonRating, 5 stars3 weeks ago
Beautiful surroundings, with the lake just steps from the door. The cabin had everything we needed for a 4 night stay. Great mix of indoor and outdoor spaces to enjoy. We absolutely loved it!
Guest favourite
Cottage in Reedville
4.89 out of 5 average rating, 46 reviews

Waterfront Bay Cottage w/ Your Own Private Beach

BrandonRating, 5 stars3 weeks ago
We had a fantastic stay at this charming cottage on a private beach! The peaceful setting and direct access to the water made for a truly relaxing getaway. We especially loved the Adirondack chairs and firepit overlooking the Chesapeake Bay—perfect for amazing views and cozy evenings. The master bedroom and living spaces offered beautiful water views that made every moment feel serene and special. The owner was incredibly accommodating with check-in and shared thoughtful, personal tips that made our stay even more enjoyable. Highly recommend this spot for anyone looking to unwind by the bay!

Private cottage rentals

Top guest favourite
Cottage in Weems
4.99 out of 5 average rating, 114 reviews

The Crab Shack

TarynRating, 5 stars6 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
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 favourite
Cottage in Topping
5 out of 5 average rating, 32 reviews

Locklies Innlet, A unique waterfront experience!

CatherineRating, 5 stars3 weeks ago
My husband and I had an absolutely wonderful time and the home played a big part in this. I was so impressed with all the extras that I just never see in other homes. The house is so cozy and such a beautiful location. Just perfect for relaxation. We will definitely want to come back. Thank you Cornelia for opening up your home to us.
Guest favourite
Cottage in Deltaville
4.83 out of 5 average rating, 181 reviews

The Little House at Waveland

AshleyRating, 5 stars1 week 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 favourite
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 favourite
Cottage in Urbanna
4.99 out of 5 average rating, 170 reviews

Little Dipper -private beach,Kayaks & paddleboards

SarahRating, 5 stars1 week 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 favourite
Cottage in Kilmarnock
4.95 out of 5 average rating, 42 reviews

Restful river house with water & golf-course view

JimRating, 5 stars3 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 favourite
Cottage in Gwynn
4.96 out of 5 average rating, 212 reviews

Mystic Seahorse Cottage & game room

MargieRating, 5 stars3 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.

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