Vacation rentals with outdoor seating in Milford

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Top-rated accommodations with outdoor seating in Milford

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Guest favourite

Apartment in Milford

4.94 out of 5 average rating, 109 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!

Aug. 28 – Sep. 4

$379 CAD per night

Guest favourite

Apartment in Milford

4.97 out of 5 average rating, 512 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!

Oct. 22 – 29

$327 CAD per night

Guest favourite

Guest suite in Fairfield

4.93 out of 5 average rating, 112 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.

Aug. 17 – 24

$209 CAD per night

Guest favourite

Guest suite in Wallingford

5.0 out of 5 average rating, 502 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

Jan. 31 – Feb. 7

$136 CAD per night

Guest favourite

Home in Milford

4.98 out of 5 average rating, 154 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!

Dec. 16 – 23

$535 CAD per night

Guest favourite

Apartment in New Haven

4.89 out of 5 average rating, 467 reviews

Fair Haven Heights Entire 1 Bedroom Apartment

Renovated and private one bedroom apartment with modern amenities within a traditional setting with amazing water views, feel like home in our cozy and nice apt with full new Kitchen ,bedroom, living room, bathroom. You can get downtown and Yale in 10 minutes by car, or 15 minutes by bus using line D that goes direct to Downtown. Convenience store, Pizza place and Wine store in the corner (five minutes walk from home), also walk to the Marina and Anastasios Boat Cafe.

Sep. 13 – 20

$194 CAD per night

Guest favourite

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your spring getaway to the Huckleberry Quarters, a totally renovated (2015) studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

Oct. 17 – 24

$223 CAD per night

Guest favourite

Home in Milford

4.93 out of 5 average rating, 121 reviews

#1 Milford Beach by Charles Island/Silver Sands Pk

Welcome to our lovely 2 bed, 1 bath unit located just across the street from a sandy beach and Long Island Sound. Explore nearby Silver Sands State Park or take a short drive to Yale University. Enjoy downtown Milford's restaurants and bars. With comfortable bedrooms, a fully-equipped kitchen, and a spacious living area, this unit has everything you need for a relaxing and unforgettable getaway. Book your stay today and experience the ultimate in coastal living!

Oct. 16 – 23

$433 CAD per night

Guest favourite

Apartment in Brookfield

4.94 out of 5 average rating, 186 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Mar. 16 – 23

$188 CAD per night

Guest favourite

Guest suite in Fairfield

4.94 out of 5 average rating, 361 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.

Feb. 23 – Mar. 2

$216 CAD per night

Guest favourite

Apartment in West Haven

4.9 out of 5 average rating, 424 reviews

! ! ! entire apartment close to the beach ! !

Come and experience West Haven and the Long Island Sound in this nice and cozy apartment close to the beach. Our apartment is complete with a full-size kitchen, bathroom, cable TV, laundry room, fresh linens, towels, air conditioning, wide driveway, and free WiFi. We will provide some FREE complimentary snacks. This apartment is ideal for single travelers, couples, and can accommodate up to three people (adults only).

Sep. 14 – 21

$255 CAD per night

Guest favourite

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

Jul. 6 – 13

$244 CAD per night