Fitness-friendly holiday rentals in Fairfield County

Private Inn

Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

Lakeview Expanse

This is a renovated house situated on 14 acres in Litchfield County, CT. This is a 5 bedroom estate - 1 king size bed, 3 queen beds, 1 bedroom is a dedicated office with a queen size air mattress. 8 guests maximum. Heated saltwater pool (closed until May 2025), 5 seater/1 lounger hot tub, 2 outdoor dining area (one on deck, other on pool patio), 8 seater dining table, 4 seater breakfast table in kitchen, extra large jacuzzi in primary bathroom, wood burning fireplace. Completely private.

Chic 1 bed Apt + Rooftop & Gym - Downtown Stamford

This luxury apartment located in Downtown Stamford will ensure you have everything you need for a wonderful stay. The property features a Fitness Center, Clubhouse, Private Rooftop Lounge with Fire Pits and Grills, and a Billiards Room. Nearby attractions: Bedford St Dining Stamford Town Center UConn Stamford Campus Latham, Mill River, and Columbus Park Avon Theatre Ferguson Library Corporate district which includes: Indeed, Harmon International, PWC, Northern Trust, Fidelity, and Frontier.

Cabin Charadora

Welcome to Your Dream Retreat! Enjoy our custom-built cabin on a scenic 5-acre lot in the Mid Hudson. With 5 bedrooms, 3.5 baths, & curated amenities, this home blends comfort & elegance for an unforgettable stay. Whether soaking in the hot tub, strolling nearby trails, or gathering around the fire pit, our cabin is your perfect home away from home. We’re proud to be in the top 1% of Airbnb listings—earned through thoughtful touches, warm hospitality & a space guests love coming back to.

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

Modern Luxe 1BR Apt in Downtown Stamford

This super clean cozy space will be your home away from home. Located in the heart of Downtown Stamford within walking distance to shopping area, restaurants and bars. 3 minutes from the I-95 and 4 minutes from the Metro North Stamford Station with easy access to NYC. This luxury apartment has all the essentials you’ll need to rest, relax and rejuvenate. Enjoy seamless check in with key lock, fast internet, and major essentials. You’ll have access to a fitness center and rooftop.

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.

The Urban & Chic Downtown Suite - reserved parking

Surround yourself with style, comfort, and sunlight. Conveniently located downtown, offering beautiful city views creating nothing but good vibes wether you are working or visiting. The apartment is light and bright during the days, and very cozy and quaint in the evenings. Comfortably sleeps 4 adults. Walking distance to shopping, theaters, restaurants, parks. Wi-Fi, reserved covered parking, workout facility and laundry room, safe friendly front desk

Designer 3BR Family Home | Backyard, Patio & Gym

Welcome to this beautifully designed 3-bedroom family home in a stunning and affluent New England neighborhood. Centrally located between Compo Beach and downtown Westport, making this updated, airy and serenely comfortable space the perfect base for families or small groups exploring the area or visiting loved ones. Enjoy the home’s spacious living areas, sunken patio, fully equipped home gym & huge backyard with plenty of room for the whole family.