Holiday rentals with a hot tub in Fairfield

4.95 out of 5 average rating, 324 reviews

Home in Cold Spring

Hilltop Hideaway Forest Villa on 13 acres!

Our artistic, spacious , comfortable home is set on 13 (fairytale-esque) private, forest acres. We are minutes away from hiking trails, swimming lakes, and the Hudson River where you can kayak. The house is located on 13 acres of land just minutes away from the vibrant shopping of downtown Cold Spring, NY. It is surrounded by lakes and hiking trails, including the Appalachian Trail. We are minutes away from the Cold Spring train station. From here, you can get to Manhattan in an hour and 10 minutes. Occasionally our two small hypoallergenic dogs are with us in the house — one toy poodle and one shih tzu. If you'd like to bring your dog(s), this is a pet friendly home! Our dogs will not stay here when you visit, of course.

5 out of 5 average rating, 145 reviews

Home in North Haven

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

4.86 out of 5 average rating, 7 reviews

Home in Newtown

Serenity by Lakefront Cottage!

Welcome to our serene waterfront cottage in Newtown CT! This tiny cottage totals 608 sqft (304 sq-ft up and down). Thoughtfully designed to be ideal for a solo getaway or a couple retreat. At our tiny cottage, you may wind down at the spa or relax over a hot/ cold beverage at the upper level deck while bird watching or observing several water vessels as they ride by in warmer weather. If you fancy water activities, you may choose to ride in our 2 seater kayak or roast s’mores by the fireplaces.

4.95 out of 5 average rating, 115 reviews

Home in New Haven

Beach Haven - waterfront, near Yale, sunsets

Everything you need for an amazing vacation, year-round, in our comfortable home right on the beach! Walk out the back door and dip your toes in the sand and in Long Island Sound. Enjoy spectacular views from the back patio, sun room, and most rooms in the house. Watch the sunset while soaking in the hot tub. Sit by the gas fireplace with a book. Stroll along the lovely nearby sea wall. 10-minute drive to Yale and all downtown New Haven has to offer. 5-minute drive to Lighthouse Point Park.

4.94 out of 5 average rating, 116 reviews

Home in Shippan Point

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

Large 4 bdr newer colonial house/w fully-equipped spacious kitchen & huge spa-like bathroom/w Jacuzzi. Just across the road from the beach, 5 min drive to NYC train & downtown Stamford. 10 min drive to Greenwich. 45 min commute to NYC. Popular/w MALS guests. 1bdr and 1 full bthr are on the 1st floor. Everything is new in the house. Spacious bedrooms, private parking. Ocean Coast Beach House is across our other listing - Nautical Fairytale Beach House. Larger groups could book both houses.

4.97 out of 5 average rating, 124 reviews

Barn in Katonah

The Magic Red Barn with heated pool now opened!

Experience country magic one hour from NYC! Our heated saltwater pool offers a perfect retreat. Enjoy nearby farmers' markets, Muscoot Farm, and scenic orchards. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn that includes: 1 king , 2 queen , and 1 toddler beds, a full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests who need to « escape ». Enjoy privacy—no other guests. Good Wi-Fi and full-house generator.

5 out of 5 average rating, 35 reviews

Guest suite in Norwalk

Cozy 1 Bd Private Entrance In-law Suite & Hot Tub

Charming Getaway in Norwalk, CT - Discover comfort and convenience in this cozy low ceiling short-term rental located just 5 minutes from local markets, dining spots, Norwalk River Valley Trail, Norwalk Hospital and shopping centers. Perfect for single travelers, work related or weekend adventurers, this space offers a warm, inviting atmosphere with modern amenities. Enjoy easy access to local attractions and scenic spots, the perfect base for exploring coastal Connecticut!

5 out of 5 average rating, 98 reviews

Home in Woodmont

Oceanfront Retreat: Modern Beach House

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

4.8 out of 5 average rating, 330 reviews

Home in Port Jefferson

The Hilltop Harborview

Guests will immediately walk past spacious hot tub into a comfortable sunroom where you’ll watch the most colorful, water view sunsets Long Island has to offer! This one of a kind offers a sprawling layout that has 3 queen size bedrooms and 1 king . We can also provide an air mattress for an additional guest. There is a kitchen equipped with stove, oven, dishwasher and washer and dryer! This beautiful walking Village has so much to offer!

4.94 out of 5 average rating, 179 reviews

Home in Stratford

Cozy Colonial - Private Hot Tub & Entire House

The way Airbnb was meant to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa, sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.

4.96 out of 5 average rating, 157 reviews

Guest suite in Guilford

Bright, Cozy Apartment in Guilford

Welcome to Guilford! Our cozy, private apartment has everything you need for a relaxing stay in Guilford. Swim in the pool or explore the hiking trails behind the property! If you'd like to explore further, we are a 10 minute drive from the center of town, and a 25 minute drive to New Haven. Featured Amenities: Pool Free Off-Street Parking Private Entrance Grill and Outdoor Seating Hiking Trails

4.96 out of 5 average rating, 333 reviews

Cabin in New Fairfield

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

Named one of the best Airbnbs in CT by Business Insider, The Little Lake Cabin is the perfect place to soak in the magic of nature by relaxing, hiking, and enjoying the lake. The cabin is a place to slow down and reconnect. Spend your days on the lake, exploring nearby towns, wineries & antique shops & your nights in the hot tub, by the fire pit roasting s'mores and gazing up at the stars.

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Holiday House Rentals with a hot tub

Home in Danbury

4.86 out of 5 average rating, 126 reviews

Private apartment

SunRating, 5 stars2 weeks ago

My stay was very comfortable and peaceful! The location was very quiet and accessible to plenty of restaurants via delivery, as well as only a ~10 min drive to downtown if desired. I was given a tour of the space when moving in since I bumped into one of the hosts, which made the move in smooth and easy to understand.

4.93 out of 5 average rating, 74 reviews

Home in Carmel Hamlet

Country getaway with pool and hot tub on 9 acres

GisselRating, 5 stars1 month ago

My friends and I wanted a weekend getaway to disconnect from everything and Calum’s place was amazing! We enjoyed our time to the fullest. Calum was a great host, easy to reach and accommodating. The only bad thing is that we should have booked more days! We definitely would love to come back on a better occasion!

4.86 out of 5 average rating, 21 reviews

Home in Croton-on-Hudson

Croton retreat w/ yard + hot tub

BenRating, 5 stars2 weeks ago

Convenient and easy! Would recommend

Home in Hopewell Junction

4.77 out of 5 average rating, 48 reviews

Great Pool, Hot Tub, Yard, Gameroom, ~1hr/ NYC

DavidRating, 5 stars1 month ago

The location is excellent and the place is very nice. However, it has fewer actual beds than are listed.

5 out of 5 average rating, 5 reviews

Home in Milford

Amazing 3BR Wildermere Beach Retreat, with Jacuzzi

MelissaRating, 5 stars3 days ago

This was my first Airbnb experience, and I was so pleasantly surprised when I arrived. It was absolutely beautifully decorated, and everything seemed to be brand new. The beds and linens were perfectly clean and comfortable. Every time I thought of something I needed, I looked and they already thought of it and had it available. Plenty of bath towels and beach towels. There was a cupboard full of board games, all of our favorites! Everything we needed for the beach…. A wagon, plenty of beach, chairs, umbrellas, and beach games for the kids. This host really thoughtfully prepared this home with everything you would need. It was a huge plus having a fenced in yard for my dog. It’s a great location for walking. Most nights we would go for long walks, grab dinner and ice cream. Thank you for a great stay!!