
Cottage vacation rentals in Milford
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Top-rated cottage rentals in Milford
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Milford cottage rentals
Cottage rentals with free parking

Rye Cottage - Walk to Beach & Playland
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.

Longview Lakehouse - 5 min walk to private beach
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.

Sunset Cabin Modern Home Kayak FirePit Lake Access
Beautiful and tidy place for a nice getaway. Host was also very responsive. Thank you!

Pumpkins & Sunflowers! Cozy Cottage in the Fall!
Had a nice stay here with a group of people attending a wedding a short drive away.

Enchanted Cottage on the Marsh, walk to beach
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.

Cozy Northern Westchester Artist/Writers Cottage
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!

Spacious Cottage Loft
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!

Ocean view cottage in Indian Neck
We always enjoy our time here, this trip was no exception. The house is comfortable, charming, and clean.
Pet-friendly cottage rentals

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

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

Private and Serene home close to I-84 and shopping
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!

Cottage in Calverton
Perfect for our weekend getaway. Very clean and relaxing and close walk to a cute little beach. We would stay here again!

Sun Filled Cottage
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

Cozy Sound-side Cottage steps from beach
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!

Charming Lake Front Cottage - Paradise Rest Home
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!

Ret's Coastal Cottage w/Private Association beach
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

North Fork Cottage
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.

Cozy Country Cottage #2
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

Welcome to Ocean’s 55 !
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.

Beautiful Boho Cottage by the beach
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.

Branford Seaside Cottage
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.

Keeler Cottage
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!

Lakefront cottage on Candlewood Lake
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.

Adirondacks in Westchester
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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- Beach
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Rye Beach
- Yale University
- Gilgo Beach
- Rye Playland Beach
- Bronx Zoo
- Cooper's Beach, Southampton
- Dunewood
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Quotonset Beach
- Robert Moses State Park
- Rye Town Beach
- Giants Neck Beach
- Seaside Beach
- Sunken Meadow State Park
- Bethpage State Park
- Woodmont Beach
- Clinton Town Beach
- Jennings Beach
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