Holiday rentals in Milford Reservoir

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Top-rated holiday rentals in Milford Reservoir

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Guest favourite

Flat in Milford

4.94 out of 5 average rating, 107 reviews

The Boathouse, private downtown Harborside suite

The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

4–11 Apr

$213 SGD per night

Guest favourite

Flat in Milford

4.97 out of 5 average rating, 510 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

14–21 Oct

$274 SGD per night

Guest favourite

Cottage in Milford

4.97 out of 5 average rating, 269 reviews

Spring Sale! Cozy Modern Rustic Cottage| Yard| W/D

Welcome to the Modern Rustic Cottage! Originally constructed in 1835 and remodeled in 2021. A designated Milford landmark, it combines modern amenities with the historic charms of wide wood plank floors, beamed ceilings, and a farmhouse kitchen. This home offers a nearly 1/2 acre backyard, on-site parking (2 cars) and W/D. Located in a charming coastal town, its adjacent to I95, approx. 1.5 -2 mile to beaches, walking distance to train/restaurants, and 15 mins to Yale/New Haven and breweries.

19–26 Sep

$267 SGD per night

Guest favourite

Guest suite in Fairfield

4.93 out of 5 average rating, 111 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

6–13 Aug

$168 SGD per night

Guest favourite

Loft in Milford

4.94 out of 5 average rating, 96 reviews

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

4–11 Jun

$172 SGD per night

Guest favourite

Flat in Bridgeport

5.0 out of 5 average rating, 40 reviews

Ricport Studio 6

Welcome to this charming Bridgeport Studio! Located downtown, near a great selection of bars and restaurants. The Arena and Amphitheater is a 6 min walk and Seaside Park & University of Bridgeport 3min Drive. This renovated industrial building features huge, beautiful, stained windows providing lots of light. A 2 min walk from Metro North and 3 min walk from Port Jefferson Ferry, you won’t find another location as convenient for the commuter. Ask as many questions as possible. Enjoy! :)

11–18 May

$155 SGD per night

Guest favourite

Home in Milford

4.98 out of 5 average rating, 153 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

28 Nov – 5 Dec

$570 SGD per night

Guest favourite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

3–10 May

$171 SGD per night

Guest favourite

Guest house in Milford

5.0 out of 5 average rating, 33 reviews

The studio downtown

The studio is a new, private, quiet, and peaceful space. It is situated on the second floor of a detached garage with a private entrance. It is located in the historic center of town, within walking distance of the train station, bars, restaurants, and beach. It is ideal for a couple looking for a beach town getaway. The studio has a king-size bed, an eating area, a kitchenette with a fridge, a sink, a double induction cooktop, a seating area, and a bathroom with a rain shower.

3–10 Apr

$179 SGD per night

Guest favourite

Guest suite in Fairfield

4.94 out of 5 average rating, 356 reviews

Private Studio Apartment; Kitchen; Fully Furnished

This 625 sqft fully furnished studio apartment has its own private entrance and sleeps 2-3 with a queen bed and Murphy bed. Other than outside, there is no contact with other people (hosts, other guests, etc) possible unless the guest allows such. The unit consists of a living room, dining space (breakfast basics provided), kitchen, full bathroom/laundry. Walk to Fairfield University; an easy train ride to NYC. Please let us know how many beds you need.

3–10 Oct

$178 SGD per night

Guest favourite

Guest suite in Milford

5.0 out of 5 average rating, 14 reviews

Modern Studio & Gamers Paradise Near Downtown

Discover endless fun at our game-filled retreat! Choose from a variety of board games, enjoy a game of bumper pool or darts, and dive into the world of video games. Minutes from Silver Sands Beach, downtown Milford, and main highways, this spacious studio features a workout area, dedicated workspace, full bathroom, kitchenette, and open layout. Perfect for a fun-filled getaway, our home ensures a blend of relaxation and entertainment in a prime location!

12–19 Feb

$166 SGD per night

Guest favourite

Home in Milford

4.89 out of 5 average rating, 19 reviews

Quiet and Cozy Getaway in Milford

Cute and well maintained cape on a quiet street in a charming beach town. Modern kitchen with breakfast island and dining table, ample outdoor seating space on both front and back porch, newly renovated basement with additional living and entertainment space, and private driveway for 2 cars. 5 min drive to Walnut Beach and Silver Sands State Park, 15 min to Yale/New Haven, and less than 90 min (~65 miles) to New York City.

3–10 Dec

$272 SGD per night