Fitness-friendly holiday rentals in Litchfield

Stylish farmhouse w/fireplace by downtown & nature

Relax and unwind in this stylish Hudson farmhouse just 15 minutes from downtown/Amtrak and 2 hours from NYC. Hudson offers acclaimed restaurants, artisanal shops, incredible hiking, and small-town charm. Enjoy this vibrant home and the many amenities it comes with: *High Speed Wi-Fi *Smart TVs *Sonos Sound System *Fully Equipped Kitchen *Fire Pit *Washer & Dryer *3 Bdrms (King, Queen, Full + Twin on Top & Futon) *Living Room & Sunroom (Bunkbed) *Multiple Work Desks & Spaces *Workout & BBQ areas

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!

Cabin Oasis in the Woods

The Cabin at Hopewell is a spacious, serene, and comfort-first home in the Hudson Valley. This 2-acre property features mature oak trees, a creek, a 2-story wrap-around deck, a heated saltwater pool (May to September!), a hot tub, and all of the amenities you need for a getaway. Newly renovated, the house features natural hardwood floors throughout, extra-large windows to bring the outdoors in, 2 working spaces, and 2 living areas. You'll love this contemporary cabin with old-school character.

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.

Lux on the River near Tanglewood w/220v EV charge

Relax with the entire family in this beautiful new home built on the Farmington River. Enjoy luxurious, natural open spaces with fireplace, full size kitchen 2 brms, walk out deck and so much to explore Within short distances enjoy entertainment to Tanglewood, Jacobs Pillow, Becket for Arts. Enjoy family friendly outdoor activities such as hiking at the Colebrook Reservoir or Kayaking on the Otis Reservoir. Don't forget about Fall Foliage and snow skiing. We are located for all diversities.

Big Deck, River Views, Mini Gym, Sleeps 8

*Inquire about discount for stays of 1 week or longer.* Riverside: 4 bedrooms, 2.5 baths: sleeps 8 in beds, dynamic riverfront access + views, high speed internet, 4 Smart TVs, AC throughout, 2 wood-burning fireplaces + fire pit (wood included!), home gym with treadmill, weight bench, stretching area, outdoor seating with grill on the deck overlooking river, kayak, basketball net, fishing poles. NOTE: Only well-experienced kayakers ought attempt the Housatonic! Pets are welcome with pet fee.

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

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.

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.