Cottage vacation rentals in Milford

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Popular amenities for Milford cottage rentals

Cottage rentals with free parking

Top guest favorite
Cottage in Rye
5 out of 5 average rating, 40 reviews

Rye Cottage - Walk to Beach & Playland

LaurenceRating, 5 stars1 month ago
Honestly cannot think of any way to improve on this place, which was perfect for our needs — and perfect for just about any scenario I can imagine. Well appointed, well located, and immaculate. I used to live in Rye, and felt immediately at home in every way. Just great.
Guest favorite
Cottage in Brookfield
4.91 out of 5 average rating, 34 reviews

Longview Lakehouse - 5 min walk to private beach

ChelseaRating, 5 stars3 months ago
Christienne was very responsive and helpful, the house was just as described and the location was so peaceful and quiet. Unfortunately I had to shorten my stay but I would absolutely be back if the opportunity presents itself.
Guest favorite
Cottage in New Fairfield
4.97 out of 5 average rating, 32 reviews

Sunset Cabin Modern Home Kayak FirePit Lake Access

FrankRating, 5 stars3 months ago
Beautiful and tidy place for a nice getaway. Host was also very responsive. Thank you!
Guest favorite
Cottage in North Fork
4.89 out of 5 average rating, 28 reviews

Pumpkins & Sunflowers! Cozy Cottage in the Fall!

DanRating, 5 stars8 months ago
Had a nice stay here with a group of people attending a wedding a short drive away.
Top guest favorite
Cottage in Branford
4.98 out of 5 average rating, 90 reviews

Enchanted Cottage on the Marsh, walk to beach

AndreaRating, 5 stars3 weeks ago
I was looking to get away for a few days and The Enchanted Cottage was just what I was looking for. The cottage was perfect for myself, had the most beautiful backyard, and was so quiet and peaceful. Bill responded to all of my questions very promptly and gave me a lot of information on walking trails around the house as well as getting around New Haven. I am very much looking forward to staying at the cottage in the future. It was the perfect getaway. Thank you.
Top guest favorite
Cottage in Katonah
4.93 out of 5 average rating, 59 reviews

Cozy Northern Westchester Artist/Writers Cottage

SabrinaRating, 5 stars10 months ago
Mark’s place is a gem, and we loved staying there. It’s very peaceful and also very close to the shops in Katonah and the train station. It’s squeaky clean and has everything you need in the kitchen if you want to cook meals. But even better is the cool artwork and the books - for sure a writer’s peaceful slice of paradise. Mark was SO nice and always quick with communications. Thanks so much for having us!
Top guest favorite
Cottage in Black Rock
4.98 out of 5 average rating, 96 reviews

Spacious Cottage Loft

MauraRating, 5 stars5 months ago
Jim’s place was an absolute gem for my inaugural trip to Black Rock! The Loft is incredibly spacious and equipped with everything you could possibly need for a perfect stay. From the moment I arrived, I was impressed by the meticulous cleanliness, attention to detail, and beautiful furnishings. Jim's communication was top-notch, making the entire experience seamless. One of the highlights was the extensive music collection, perfect for setting the mood during my downtime. The bed and furniture provided a level of comfort that made it hard to leave. Nestled on a serene, tree-lined street, the location couldn’t be better; it’s just a leisurely stroll away from delightful restaurants, charming shops, food markets, and more. I can’t wait to return for another stay whenever I’m in the area!
Guest favorite
Cottage in Branford
4.97 out of 5 average rating, 70 reviews

Ocean view cottage in Indian Neck

SaraRating, 5 stars2 weeks ago
We always enjoy our time here, this trip was no exception. The house is comfortable, charming, and clean.

Pet-friendly cottage rentals

Guest favorite
Cottage in North Fork
5 out of 5 average rating, 13 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

ChristinaRating, 5 stars3 weeks ago
Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!
Guest favorite
Cottage in Norwalk
4.94 out of 5 average rating, 68 reviews

Seaside Serenity: 2B 1B, Patio,Near Beach

AdamRating, 5 stars3 weeks ago
We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!
Guest favorite
Cottage in Newtown
4.93 out of 5 average rating, 244 reviews

Private and Serene home close to I-84 and shopping

Samantha Lancisi Rating, 5 stars1 day ago
Saverio’s place was just as listed. We needed a place to stop and rest for the evening and his place is just what we needed!
Superhost
Cottage in North Fork
4.91 out of 5 average rating, 53 reviews

Cottage in Calverton

KaitlynRating, 5 stars8 months ago
Perfect for our weekend getaway. Very clean and relaxing and close walk to a cute little beach. We would stay here again!
Guest favorite
Cottage in Southbury
4.94 out of 5 average rating, 18 reviews

Sun Filled Cottage

Talitha SeifertRating, 5 stars1 month ago
My husband and I stayed at the cottage for 3 months and enjoyed our time very much. We were very happy from every perspective: The cottage had all the equipment we needed and wished for. We sometimes used the fireplace and loved the bed/couch. The cottage is perfect to rest and focus. We enjoyed to have so much nature around us. We took a walk in the close park with a lake almost every day. We liked to live at a small farm with dogs, chicken and goose. Debbie and Kirk were always there when we needed them and also made us internationals feel welcome. They explained and helped us proactively e.g. changed regional weather circumstances. We also regularly got eggs from the chicken what was always a nice surprise. Communication/ interactions were always easy and friendly. I recommended my work to plan future stays for assignments in this Airbnb. In our opinion it is better than a hotel: Very comfortable, cozy, close to nature and a special American experience. Thanks a lot Debbie and Kirk
Top guest favorite
Cottage in North Fork
4.87 out of 5 average rating, 92 reviews

Cozy Sound-side Cottage steps from beach

ChristopherRating, 5 stars4 months ago
We had a great experience staying at Melissa’s cottage and would happily recommend it to anyone else! We were in town from Florida visiting family in Rocky Point for Christmas and chose Melissa’s property as our place to stay. Melissa was very communicative, check in was super easy and we felt right at home on her property. Would definitely consider staying here again. Thanks Melissa!
Superhost
Cottage in South Salem
4.84 out of 5 average rating, 45 reviews

Charming Lake Front Cottage - Paradise Rest Home

DeborahRating, 5 stars6 days ago
Super special place. Very peaceful. Beautiful surroundings. If you love nature and a charming location, this is the place. The host was also extremely responsive and the cottage had everything I needed for a three month stay! Highly recommend!
Guest favorite
Cottage in Branford
4.96 out of 5 average rating, 46 reviews

Ret's Coastal Cottage w/Private Association beach

LauraRating, 5 stars1 week ago
Thank you !! We enjoyed our stay. The home is lovely and the area was so convenient to all ! The airport is 7 minutes away. Def would stay here again. Thanks again

Private cottage rentals

Cottage in North Fork
4.75 out of 5 average rating, 315 reviews

North Fork Cottage

GailRating, 5 stars1 week ago
Rich’s cottage was very comfortable for me and my 2 friends who came for a weekend winery getaway. The kitchen looked newly renovated and each of the bedrooms were comfortable. Also, the cottage had a nice deck in the back to relax on. Location was a short walk to a public beach and driving distance to many restaurants and wineries. We had a great stay.
Top guest favorite
Cottage in Miller Place
4.99 out of 5 average rating, 131 reviews

Cozy Country Cottage #2

BethRating, 5 stars1 week ago
The host was very responsive and very helpful. The house is absolutely adorable. It was spotless had everything you need to make it feel like it was Home. Great selection of kcups. Easy to get pretty much anywhere. The neighborhood and surrounding area is absolutely beautiful. The water is gorgeous Patchogue, Greenport, the beaches, all very close. Had a great time and will definitely be where I stay when I come home to Long Island
Top guest favorite
Cottage in Woodmont
4.98 out of 5 average rating, 89 reviews

Welcome to Ocean’s 55 !

MaqCRating, 5 stars5 months ago
We lived in Joseph’s fantastic place as a team of 4 chaperons and 7 teenagers attending the tournament of champions at Yale University. Everything about this listing is fantasy - proximity to the beach and amenities, the decor, furniture and fixings, and Joseph’s super speed in response and guidance. Every one of us was stoked and it’s a place we’d love to come back to and call home again after a while.
Superhost
Cottage in Rocky Point
4.76 out of 5 average rating, 42 reviews

Beautiful Boho Cottage by the beach

StephRating, 5 stars4 months ago
Staying at Fabiola's was a dream. This place is very homey and welcoming. We had a lovely stay for Christmas with family, walking to the beach in the morning and cozying up around the fire in the evening. The kitchen is well stocked for cooking, the beds were comfortable, and our dog loved the fenced in yard. Would love to stay again.
Cottage in Branford
4.83 out of 5 average rating, 18 reviews

Branford Seaside Cottage

AprilRating, 5 stars9 months ago
If you love an escape from the city and want to be near the peacefulness of Branford and the Long Island sound this is a perfect little cottage to get away with your furry friend. The location is just across the street from the beach and the sea and the cottage is comfortable. Tricia was helpful, responsive and easy to work with.
Top guest favorite
Cottage in North Salem
4.98 out of 5 average rating, 330 reviews

Keeler Cottage

LouRating, 5 stars19 months ago
Hilary was such an amazing host. Friendly and so welcoming! Very lucky to have been able to stay at her cottage…. The cottage was amazing , clean, quiet and cozy! Looking forward to her opening up her own bed and breakfast. Truly an amazing host!
Cottage in Danbury
4.84 out of 5 average rating, 19 reviews

Lakefront cottage on Candlewood Lake

AlexRating, 5 stars11 months ago
This cottage was the perfect stay for our long weekend! Great views of the lake and a nice place to hangout and enjoy the beautiful weather.
Guest favorite
Cottage in Pound Ridge
4.94 out of 5 average rating, 202 reviews

Adirondacks in Westchester

HayatiRating, 5 stars4 months ago
it was a great place, felt amazing with great lake view and access. heating system works perfect very comfortable place. has everything you need, full kitchen full house, clean sheets bed clothes towels everything was perfect

Quick stats about cottage rentals in Milford

  • Total rentals

    20 properties

  • Nightly prices starting at

    $120 before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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