Holiday houses in Milford Reservoir

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Top-rated holiday rentals in Milford Reservoir

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Guest favourite

Apartment 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 July

$3,427 AUD total

Guest favourite

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

24 Feb – 3 Mar

$1,524 AUD total

Guest favourite

Apartment in Milford

4.97 out of 5 average rating, 508 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!

25 Sept – 2 Oct

$2,583 AUD total

Guest favourite

Cottage in Milford

4.97 out of 5 average rating, 268 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 July

$3,873 AUD total

Guest favourite

Guest suite in Fairfield

4.93 out of 5 average rating, 110 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.

22 – 29 Oct

$1,607 AUD total

Guest favourite

Apartment in Bridgeport

5.0 out of 5 average rating, 6 reviews

Ricport Studio 5

This little studio is the perfect shut in. An electric fire place, with a curved smart TV, complimented by handmade industrial colored windows, makes this place dangerous for letting time fly. To help the space open up, we installed a Murphy bed (that should be handled with care). Theres no doubt you’ll feel comfortable and at home as soon as you arrive. Located 2min from Metro North/Amtrak, 4min from Port Jeff. ferry, 5min from Arena/Theater, 6min Park/Beach, Downtown, near it all. Ask Parking

30 Apr – 7 May

$1,355 AUD total

Guest favourite

Apartment in Milford

5.0 out of 5 average rating, 48 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

13 – 20 Sept

$2,089 AUD total

Guest favourite

Loft in Milford

4.94 out of 5 average rating, 94 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.

13 – 20 Jan

$1,630 AUD total

Guest favourite

Home in Milford

4.98 out of 5 average rating, 152 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!

21 – 28 Nov

$4,633 AUD total

Guest favourite

Guesthouse in Milford

5.0 out of 5 average rating, 32 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.

19 – 26 Oct

$1,725 AUD total

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!

20 – 27 Sept

$2,106 AUD total

Guest favourite

Apartment in Milford

4.95 out of 5 average rating, 75 reviews

Downtown, Private balcony, 1gb fiber Wi-Fi

Charming 2nd floor one bedroom apartment with a separate entrance located in Milford's Historic district south of the green. You'll be 0.4 miles to the Milford train station. It's only 0.3 miles to the Milford Green which features restaurants, nightlife, and the Milford Harbor. Three local breweries are within 20 minutes of driving. Enjoy 17 miles of coastline where you can swim, kayak, and paddle board. Check in time is flexible with self check in lockbox.

4 – 11 May

$2,020 AUD total