Vacation rentals in Milford

4.93 out of 5 average rating, 267 reviews

A scenic beach scene captures individuals enjoying a relaxing day by the water. Sun loungers are positioned in the soft sand, with gentle waves lapping at the shore and a vibrant blue sky filled with fluffy white clouds.

Cottage in Guilford

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

4.92 out of 5 average rating, 205 reviews

A private backyard space features a wooden gazebo with a seating area, surrounded by a gravel surface. Comfortable wicker furniture, including a sofa and chairs, invites relaxation. The fenced yard offers a sense of privacy, complemented by beach gear visible in the background.

Guesthouse in Milford

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

5 out of 5 average rating, 10 reviews

Home in Roxbury

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

4.79 out of 5 average rating, 43 reviews

Two comfortable chairs are positioned on a spacious porch, offering a clear view of the beach and ocean. The horizon is visible in the distance, with calm waters under a blue sky dotted with clouds.

Home in West Haven

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

4.96 out of 5 average rating, 210 reviews

A bright and airy sunroom features large windows that allow natural light to fill the space. A cozy daybed is positioned beside an accent table, while two white wicker chairs add additional seating. Subtle decor elements enhance the inviting atmosphere.

Home in Milford

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!

5 out of 5 average rating, 102 reviews

A cozy cabin nestled among trees is shown at dusk, with warm light streaming from the windows. An outdoor fire pit is visible, adding an inviting glow to the natural surroundings. Tall trees frame the scene, enhancing the tranquil atmosphere.

Cottage in South Salem

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

4.93 out of 5 average rating, 135 reviews

A rustic seafood shack features a prominent sign reading 'Lobster Landing'. The white facade is complemented by red accents, and outdoor seating is visible alongside a wooden fence. Clear skies and a few scattered clouds enhance the setting's open, inviting feel.

Home in Clinton

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views of River. Convenient to beaches, and includes free pass to the Clinton Town Beach! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to groceries, coffee shops and amazing CT scenery! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants with music, and lots more.

4.88 out of 5 average rating, 188 reviews

Home in New Milford

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

4.92 out of 5 average rating, 116 reviews

Home in New Fairfield

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

5 out of 5 average rating, 101 reviews

Home in Milford

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

4.94 out of 5 average rating, 113 reviews

Cottage in Plymouth

Lakefront Cozy Oasis 2BR w/ stunning sunset views

It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits

4.84 out of 5 average rating, 154 reviews

Home in Stamford

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

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A space thats all yours, with room for everyone

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Popular amenities for Milford vacation rentals

Self check-in

Pet friendly

Laptop-friendly workspace

Hot tub

Gym

Stay near Milford's top sights

Stop & Shop47 locals recommend

Trader Joe's45 locals recommend

Stonebridge Restaurant43 locals recommend

ALDI35 locals recommend

Connecticut Post Mall31 locals recommend

The Greek Spot Cafe & Grill28 locals recommend

Pet-friendly vacation rentals in Milford

4.93 out of 5 average rating, 319 reviews

An inviting outdoor patio area is featured, shaded by a wooden structure. Decorative string lights hang overhead, while a variety of seating options are provided. Lush greenery and orange lilies enhance the landscaped garden, creating a peaceful and tranquil setting.

Guesthouse in Southbury

Charming Guest Cottage with Modern Amenities

4.89 out of 5 average rating, 485 reviews

A serene outdoor view showcases a driveway framed by lush greenery and trees displaying vibrant yellow leaves. The ground appears damp from recent rain, and fallen leaves are scattered along the path, emphasizing the seasonal transition.

Cabin in Rocky Point

Great little place just for a couple

4.98 out of 5 average rating, 101 reviews

A serene view of Long Meadow Pond is presented, bordered by sandy areas and lush trees. The calm waters reflect the bright blue sky and distant foliage, offering a tranquil setting for outdoor activities. The scene captures a peaceful lake environment ideal for swimming and kayaking.

Cottage in Bethlehem

Cozy Getaway | Pet Friendly | Litchfield Cty

The exterior of a modern farmhouse is displayed, featuring white siding and a combination of one and two stories. A spacious porch with a railing overlooks the surrounding landscape, while various plants are arranged near the house. Clear skies and sunlight illuminate the setting.

4.97 out of 5 average rating, 146 reviews

Secluded Farmhouse - Studio Apartment Style Unit

A single-story brick house is set amidst a lush green lawn, framed by colorful flowers and bushes. A pathway leads to the front entrance, with a chimney visible on the right side. Tall trees provide shade in the background under a clear blue sky.

4.95 out of 5 average rating, 103 reviews

Walk to Vineyards, Beach, Restaurants • Sleeps 8

4.92 out of 5 average rating, 118 reviews

A cozy studio apartment is showcased, featuring a spacious bed with light blue bedding. A comfortable gray sofa is positioned nearby, adorned with a patterned throw pillow. Natural light enters through a window framed by light blue curtains, highlighting a decorative wall shelf with personal items.

Apartment in Middlebury

Cozy Apartment with Water View of Brook

Apartment in Carmel-by-the-Sea

A well-maintained private yard features lush green grass, a vibrant hammock for relaxation, and a stone path leading through flower beds. A cozy seating area with woven chairs and a decorative rug is positioned near the apartment, surrounded by trees for added privacy.

4.87 out of 5 average rating, 297 reviews

Private space, with yard

4.97 out of 5 average rating, 106 reviews

A serene river view is framed by tall trees, creating a natural canopy overhead. In the foreground, two Adirondack chairs are positioned on the grassy bank, inviting relaxation while overlooking the calm water surrounded by lush greenery.

Home in New Milford

Idyllic retreat on the water <1.5 hrs to NYC.

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Vacation rentals with jacuzzis in Milford

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

4.81 out of 5 average rating, 319 reviews

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

The Hilltop Harborview

4.96 out of 5 average rating, 501 reviews

A flowering tree with cascading pink blooms stands in a lush green yard. The vibrant flowers contrast with the wooden exterior of the house in the background, which features large windows and a warm architectural design. The scene is well-lit, conveying a serene outdoor environment.

Home in Wading River

Your Zen Retreat

4.95 out of 5 average rating, 177 reviews

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

5 out of 5 average rating, 223 reviews

A whimsical hobbit house is nestled within lush greenery, featuring an arched, stone roof and vibrant red entrance. Two rounded windows frame the doorway, surrounded by a beautifully landscaped yard with a stone path leading to the entrance.

Home in Pawling

Hobbit House of Pawling

4.94 out of 5 average rating, 115 reviews

Sailboats glide across a calm blue sea, with distant shorelines visible under a clear sky. The tranquil waters reflect shades of blue, creating a serene nautical setting that accentuates the beauty of the surrounding landscape.

Home in Shippan Point

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

4.96 out of 5 average rating, 324 reviews

Cabin in New Fairfield

The Little Lake Cabin— hot tub, fire pit, & kayaks

4.88 out of 5 average rating, 102 reviews

A cozy living area is furnished with two armchairs featuring floral patterns and colorful cushions. A wooden coffee table rests on an area rug, and a brick fireplace is situated beneath a wall-mounted clock. Large windows allow natural light to illuminate the space.

Apartment in Brewster

The Hideaway

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House rentals in Milford

A light-filled living area features a neutral-colored sofa alongside a blue couch, with decorative pillows adding subtle color. A wooden coffee table rests in front, and large windows with bamboo shades allow natural light to brighten the space.

4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

4.89 out of 5 average rating, 101 reviews

The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.

Home in East Haven

Welcome To Piper's Rest

5 out of 5 average rating, 133 reviews

A single-story home is situated on a well-kept lawn with lush greenery and small bushes lining the front. The exterior features light-colored siding and a dark roof, complemented by multiple large windows that enhance natural light.

Home in Cheshire

Pool House

4.94 out of 5 average rating, 32 reviews

A spacious outdoor area is visible, featuring a winding path that leads through a grassy landscape. Trees of varying heights frame the view, capturing seasonal colors with a backdrop of rolling hills under a clear blue sky.

Home in New Milford

Serene Country home 24 mi Mohawk ski area

4.93 out of 5 average rating, 107 reviews

The living area features a dark grey sofa adorned with decorative pillows, positioned on a textured area rug. A small wooden side table stands next to the sofa, and a framed landscape artwork hangs on the wall. A dining area is visible through the doorway.

Home in Fairfield

Downtown Fairfield 3 bedroom Colonial

4.97 out of 5 average rating, 60 reviews

A spacious living area features a gray sectional sofa and a glass coffee table resting on a patterned rug. Natural light is provided by large windows, enhancing the bright, airy environment. A television is positioned on a dark wooden media stand, complementing the hardwood flooring.

Home in Southington

Large 1st floor of duplex in town center

4.93 out of 5 average rating, 157 reviews

A dining area features a round black table surrounded by six wooden chairs, creating an inviting space for meals. Decorative artwork hangs on the walls, and natural light filters through two windows, enhancing the room's brightness.

Home in Mamaroneck

3 Bed/2 Bath Private Home in Mamaroneck