Holiday rentals with a pool in Litchfield County

Moody Pond House: Weekend Country Escape

Brand new family friendly modern home with in-ground gunite pool set on 18.5 acres with a large pond and adjacent to 150 acres of protected land. 5 minute drive from Lake Waramaug, a 2 minute drive from Hopkins Vineyard and 15 minutes from The Mayflower Hotel. Situated conveniently between the historic towns of New Preston and Kent this home provides everything you need for a relaxing stay including fully stocked kitchen, outdoor dining table, gas grill, fire pit, hiking on property & much more.

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Serene, elegantly appointed 19th century compound, fully modernized and set on the edge of a 50 acre land preserve next to boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this expansive home has four buildings and every amenity: pool, hot tub, heated gym, cedar sauna, central AC, 2 chef’s kitchens, game barn, primary suite with wb fireplace and soaking tub, a pool house guest suite with steam shower, & treehouse w/ slides & a swing set built on a 300yr old oak tree.

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

Our peaceful, skylit, 3-bed 2-bath lodge is a totally private woodland paradise on a quiet country lane. Part secluded retreat, part rustic resort, part '70s-style cottage, it's only 2 hours from NYC & 20 minutes from Hudson. Unwind in 50 acres of untouched forest & grounds, a seasonal saltwater pool & cabana bar, a Finnish sauna & 7-person hot tub (open year-round), an open chef's kitchen & living room, & a sunny deck overlooking endless natural splendor. See more @sunbeamlodge on Instagram.

Artist Retreat in Beautiful Country Setting

Stay at this unique property, owned and designed by a Eu artist, and enjoy the quiet countryside and natural beauty that rural CT has to offer. A large one bedroom studio with an modern fireplace, is equipped with a comfortable king size bed, full bathroom, sauna, indoor resistance pool- available at an extra charge, kitchenette, a workspace, and high-speed internet for seamless remote work. Relax in the evening at your own private outdoor seating area surrounded by the property's charm.

King 1BR Apt with Cozy Den and Luxury Amenities

This gorgeous apt, located in a brand-new luxury building at the center of New Haven’s historic downtown, offers unparalleled comfort, service, and amenities. You can watch a movie on a 65" HDTV, work in one of 5 co-working spaces, or relax at the pool w/ grills and cabanas. Highlights: • Walkable access to Yale • Deep-clean prior to every guest • Coffee, fresh linens, and bathroom essentials • 24/7 fitness center • Rooftop sun terrace + grills • Entertainment lounge w/ bowling alley

Mountaintop Horse Farm with Pool

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

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.