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Cottage holiday rentals in Middlesex County

Find and book unique cottages on Airbnb

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Popular amenities for Middlesex County cottage rentals

Cottage rentals with a hot tub

Top Guest favourite
Cottage in Burlington
4.98 out of 5 average rating, 112 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

Mary-CatherineRating, 5 stars1 week ago
Just as listed...small cottage by the water and the view was stunning! I liked relaxing in the swim spa or by the calming lights and sounds of the fake electric fire-- definite cozy vibes! The kitchen is clean and well stocked with utensils etc. Feyza was great about checking in. Thanks!
Superhost
Cottage in East Hampton
5 out of 5 average rating, 3 reviews

East Hampton: Close to The Village and The Beach

JimmyRating, 5 stars7 months ago
I had a wonderful weekend at Andrew’s place in East Hampton. It was gorgeous, perfect location, perfect layout, and such a central location to everything. It was incredibly clean and organized and the backyard was beautiful for relaxing. Andrew was also a terrific host- he left us beverages, was super communicative and flexible and I’m so happy I stayed here. Hopefully I’ll rent again soon!!
Superhost
Cottage in Amagansett
4.87 out of 5 average rating, 23 reviews

4 Br Beach House; Short Walk to Beach!

EveRating, 5 stars4 months ago
Beautiful large home, clean linens, plenty of towels, bathtub worked great. John was very responsive and helpful. Slept 9 people comfortably. The living room area was cozy with an indoor fireplace and the kitchen was large with a large oven and dishwasher. Five minute easy walk to a beautiful quiet beach. Highly recommend this place.
Top Guest favourite
Cottage in Plymouth
5 out of 5 average rating, 13 reviews

Summer Escape w/ Cool Tub + Lake Access

AnanyaRating, 5 stars2 weeks ago
Our family of five loved staying at Yoka and Val's place. The location is very quiet with a peaceful pond across the street. The house itself is very clean and comfortable with everything you need - towels, soap, shampoo, conditioner, coffee and spices - easily available. The beds were also very comfortable. The best part, of course, was the private hot tub in the back yard. It was set in a canopy for extra privacy and wind protection. We loved it. We would definitely stay here again if in the area.
Guest favourite
Cottage in Bridgehampton
4.97 out of 5 average rating, 87 reviews

Bridgehampton Cottage Close to Town, South of HWY

ChancellorRating, 5 stars3 days ago
Wow!! The perfect peaceful getaway that is close to everything!! Tucked away off the road the house is quiet with a beautiful yard. The interior is both stylish and comfortable. The kitchen is extremely well outfitted. Andrew is a great host and an excellent communicator. We only wished we could have stayed longer!! The question isn’t will we come back, it’s simply when!
Cottage in Cutchogue
4.69 out of 5 average rating, 195 reviews

Lovely 2 BR Beach House No. Shore

KateRating, 5 stars6 months ago
Great spot for a long weekend! Wonderful location close to the beach and local wineries. Richard was a great host offering lots of recommendations and clear instructions for check in and using available amenities.
Cottage in Old Lyme
4.82 out of 5 average rating, 218 reviews

Private Beach Cottage

BillRating, 5 stars1 week ago
This well-appointed space is perfect for two people. Old Lyme is justly famous for its Florence Griswold Museum, as well as one of the better historic main street walking tours. (Currently, there's an exhibit at the museum about Old Lyme's slave-owning past.) And, then, of course, there's the ocean. Remember to ask your hosts about their beach parking pass. P.S. You may also need to bring your own coffee for the drip system.
Guest favourite
Private room in Hampton Bays
4.8 out of 5 average rating, 97 reviews

Private Room in the House that Art Built

BohdannaRating, 5 stars7 months ago
The place was charming, quaint, and exactly as described. It had a cozy vibe that made it feel like a home away from home. The location was perfect, with easy access to everything I needed. The host was incredibly responsive and helpful throughout my stay. Highly recommend this spot for anyone looking for an enjoyable experience!

Pet-friendly cottage rentals

Guest favourite
Cottage in East Hampton
4.89 out of 5 average rating, 35 reviews

Charming 3 bedroom cottage on Lake Pocotopaug

AnnRating, 5 stars7 months ago
The house was perfect. I felt right at home. Beautiful views. 5 min from town and my family. A view of East Hampton I have never seen. Host was easy to get a hold of. It was a home away from home. I plan to stay again if available when i need it.
Guest favourite
Cottage in Guilford
4.95 out of 5 average rating, 80 reviews

Direct Shoreline Long Island Sound Waterfront

ThomasRating, 5 stars7 months ago
Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.
Cottage in Westbrook
4.83 out of 5 average rating, 12 reviews

Charming New Beach Cottage

BethanyRating, 5 stars9 months ago
Looks can be deceiving in the best possible way. Although the house looks tiny, it was very spacious for my family of four. The beach was the perfect distance from the house. A wonderful time on this vacation.
Guest favourite
Cottage in Deep River
4.91 out of 5 average rating, 23 reviews

Serene Waterfront Cottage

RobertRating, 5 stars5 months ago
As always, we love our stay at the cottage. It’s becoming our home away from home when visiting our son. Thanks for all our goodies! Always a great surprise! Have a wonderful Christmas. We’ll see you next year I hope.
Guest favourite
Cottage in Guilford
4.87 out of 5 average rating, 38 reviews

Your own Thimble Islands private cottage!

MichaelRating, 5 stars4 days ago
Everything about this stay was as near too perfect as possible. First Sean was proactive, quickly responded to any questions and his pre-visit communications were comprehensive. The pictures accurately describe the house but in reality, they do not do it justice. There are water views from every window. The place and views are amazing!! It is just what we were looking for, on the ocean, private and peaceful. Short drive to the village with shops and restaurants. Highly recommend for a couple who is looking for an escape, you will not be disappointed
Superhost
Cottage in Westbrook
4.52 out of 5 average rating, 21 reviews

Remodeled Cottage Private Old Kelsey Point Beach

JillRating, 5 stars9 months ago
Cheryl's place was adorable! I felt right at home in the cosy open concept living space. My mom crashed the weekend portion of the trip which was nice. My cat Mushu had a wonderful time and we even went outside. The beach was about a four minute walk for me, and a breathtaking view as you approach. Cheryl had everything necessary and mentioned. Next time I'll be sure to bring coffee filters and sugar. There were unexpected amenities too like paper towels and trash bags, and candles. There were also tons of spare toiletries like shaving cream and shampoo and conditioner and body wash. Thanks again!
Cottage in Guilford
5 out of 5 average rating, 4 reviews

SanctuaryCottageByTheSea-Kids, Pets, Waterfront

ChristelRating, 5 stars19 months ago
What an incredible experience! Was a bit hesitant after reading pets were allowed as one of our friends is allergic to dogs and cats - the cottage was super clean and no sign that a “furbaby” had ever been there. Had a personalized welcome letter for our party of 6, and favorite beverages thanks to advance questions and special touches from Mickey. Loved listening to the waves, reading by the fire and getting in a game of ping pong at the outdoor table. Every detail has been considered from the 3 charging stations to the guidebook and more. There are positive quotes and signs in the cottage and we were so relaxed and recharged. Will definitely book again. 5 stars all around! Thank you.
Cottage in Old Saybrook
4.89 out of 5 average rating, 35 reviews

Luxury Driftwood Cottage @ Saybrook Point

CherylRating, 5 stars7 months ago
We loved staying at Allison’s cottage! We were attending a wedding at Saybrook Point Inn and the cottage was a 2 min walk which made it so convenient! The home was decorated in a cozy, beach style with a private, fenced in backyard. Alison was very welcoming to us and our two doodles. It was great to have them with us. I highly recommend this Airbnb!

Private cottage rentals

Superhost
Cottage in Portland
4.61 out of 5 average rating, 18 reviews

Lake Cottage Getaway

NanaRating, 5 stars6 months ago
Had a really wonderful time here for my friends’ trip. Kimberly was a communicative and amazing host, and the cottage was clean and well-stocked. The location is also perfect if you are hoping to enjoy some peace and relaxation, with nearby parks and trails available for exploration.
Top Guest favourite
Cottage in Guilford
4.99 out of 5 average rating, 97 reviews

Waterfront Joshua Cove Cottage with private beach.

FrankRating, 5 stars5 months ago
We spent Thanksgiving in the beautiful Joshua cottage. This was one of the best Airb&b stays we have ever had. The hosts were wonderful- making sure we had everything we needed. The spot directly on the water is magical.
Top Guest favourite
Cottage in Madison
5 out of 5 average rating, 28 reviews

Charming Madison, CT Carriage House ocean rental

KellieRating, 5 stars4 months ago
Wonderful host, great location, absolutely loved our stay!
Cottage in Old Saybrook
4.86 out of 5 average rating, 7 reviews

Seasonal Quaint Beach Cottage short walk to beach.

JustineRating, 5 stars8 months ago
One of the best places I have stayed! Grew up staying in the cottages in that area and it was a trip down memory lane. Christine was super friendly and helpful. Loved that she shared this space with us! Close to the beach and great local restaurants with the best seafood!
Cottage in Old Saybrook
5 out of 5 average rating, 4 reviews

Cornfield Point Beach Cottage

DerekRating, 5 stars8 months ago
My wife and I really enjoyed the house. Beautifully remodeled with all the amenities you would need. Plus all the extras for a great beach vacation. The deck was great for morning coffee and it had a gas fire “pit” to enjoy a glass of wine at night. The outdoor shower is a great added bonus. Wonderful walking neighborhood with beautiful scenic overlooks. Short walk to the beach. Many restaurants and quant shops within 5 minutes ride. All in all this is a great place to spend a summer vacation on the Connecticut shore.
Top Guest favourite
Cottage in Guilford
5 out of 5 average rating, 30 reviews

Waterfront Cottage With Unforgettable Views

LelandRating, 5 stars5 months ago
The cottage was every bit as charming as the listing. Quiet, clean, updated, and surrounded by beautiful views. We used this as our home base while visiting family in the area for Thanksgiving and it accommodated our family of 5 no problem. It’s cozy but has everything you need.
Guest favourite
Cottage in Old Saybrook
4.81 out of 5 average rating, 27 reviews

Charming Old Saybrook Cottage < 1 Mi to Beach

LouRating, 5 stars3 weeks ago
Very nice home in a great location near the river and ocean. We attended a wedding at Saybrook Point Inn, so this was the perfect location. Host was very responsive and home was as described. Would stay here again.
Cottage in Hebron
4.57 out of 5 average rating, 21 reviews

Cozy 3 bd Cottage w/ access to private lake

AmandaRating, 5 stars2 weeks ago
We very much enjoyed our stay on Amston Lake! We are always looking for comfortable places for our 3 person family to stay near relatives in Colchester CT. Amos' place fit the bill! The beds were comfortable, the amenities perfectly met our needs and the home was very comfortable. My only regret is that we were out visiting most of the time and did not get to spend enough time enjoying the beautiful lake and natural surroundings! We are likely to return.

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