Luxury rentals in Connecticut River

The Bluff: Designer | Views | Pool | Hot Tub

The Bluff at Eagle Hollow is a 3 bed, 2.5 bath modern haven just 2 hrs from NYC overlooking the Hudson River. Boasting floor-to-ceiling windows throughout and two decks to enjoy the stunning river views, this home is the definition of effortless style. Lounge by the pool, relax in the hot tub, get cozy by the fire pit or simply take in the views from multiple spots. Nearby towns: Marlboro (5mins), Poughkeepsie (15mins), Newburgh (20mins), Beacon (25 mins), New Paltz (25mins), Kingston (35mins)

Casa Catskills: Luxury, Modern 9 Acre Escape

Escape to Casa Catskills, a modern, luxury mountain retreat on 9 private acres just 10 mins from Hunter & Windham Ski Resorts. The home’s amenities include a theater room, hot tub, pool table, indoor & outdoor fireplaces, fully equipped kitchen with PFAS-free cookware and dedicated office space with beautiful mountain views. Enjoy 6 serene bedrooms (3 kings, 2 queens, 2 twins) and 5 spa-like bathrooms with radiant floors. Perfect for a wellness reset or city getaway. VIP services available.

Upstate Retreat 1+Hr NYC ~ Pool, Padel and Views

Escape to a serene hillside retreat on 23+ acres with breathtaking views of the Hudson Valley. Just over an hour from NYC, this luxurious estate is perfectly located for outdoor adventures and local delights, including orchards, wineries, skiing, and hiking. Unwind on the patio, play games in the barn, or relax by the fire. Whether you're hosting friends, family, or celebrating a special occasion, this spacious home blends rustic charm with modern comforts for an unforgettable getaway.

Oceanfront Stunner | 15 Min to Portland | NewBuild

Welcome to Driftwood Shores — a stunning, 5,500 sq ft custom-built coastal retreat where modern architecture meets classic Maine waterfront living. Built in 2025, this luxury home offers panoramic Casco Bay views, direct access to the ocean and an unparalleled location. Designed for gatherings of all sizes, this home is perfect for multigenerational trips, reunions, or groups looking to experience Maine in style. 15 Minutes to Portland's Old Port 20 Minutes to Freeport Outlets & Shops

Meadow View Manor | 17,000sqft w/ Olympic Pool

Nestled on expansive private grounds in Barrington, NH, this 17,000+ sq. ft. estate is designed for those who appreciate luxury, privacy, and world-class amenities. Featuring breathtaking views of rolling fields and the majestic Nippo Mountain, expansive entertaining spaces, and a heated Olympic-size indoor pool and sauna, this property is ideal for small intimate weddings, family reunions, corporate retreats, or simply as a serene escape from everyday life.

Luxury 4BR Chalet/Hot Tub, Sauna + Shuttle Access

Salty Margarita | Luxe Chalet w/ Hot Tub, Sauna, Game Room & More Gather, unwind, and play at Salty Margarita—Stowe’s ultimate group getaway. This 4BR/4BA chalet features fireplaces in every bedroom, a ski-lift bench in the mudroom, a hot tub, cedar sauna, game room with pool & ping pong, plus luxe linens & special touches throughout. Steps from the shuttle, bike path & breweries, it’s perfect for families and friends. Concierge services available!

Modern retreat, Catskill views from Pool & Hot Tub

Enjoy stunning views of the Catskills! Set on 32 acres, located close to the Taconic Pkwy & only 5 mins from Chatham. 7 person salt water hot tub open year round + infinity edge pool with large hot tub open May to Nov. The house has a 14 person dining room table and can accommodate up to 14 people with: 4 bedrooms; 1 study with a convertible couch; & 2 Murphy beds. Additional fee above 8 guests. ADULTS ONLY. Inquire if dates aren't available!

The Charles Château Private Estate

Unique and distinctively remodeled home encompasses modern luxuries with the characteristics of a French chateau, just moments away from Boston. This is a luxurious property built to offer a memorable experience with entertaining amenities for fourteen guests. Every detail has been considered, filled with natural light from all the large windows, furnished by Restoration Hardware, Viking Appliances, Quality Linens and many other high-end luxuries.

Potter Mountain House: New Catskills Luxury Estate

Click: "Show more" to read full description. Stay in a newly restored 19th-century Greek Revival church in the high peaks of the Northern Catskills. Just 20 min to skiing at Windham Mountain! Potter Mountain House offers panoramic views from nearly every room with soaring ceilings, original wood beams, gas fireplace, chefs kitchen, office, a walk-in wine room and library within the steeple and four serene bedrooms and spa-like bathrooms.

Whimsy Woods - 14 Acre Millbrook Estate with Pool

Whimsy Woods, where contemporary design meets country escape, is a private getaway just minutes from the village of Millbrook. Approaching the property, you’ll feel the rich equestrian history of this historic hamlet, with paddocks and stables, sprawling meadows, and lush lawns. Through the wooden gate, find this uber-private 14-acre estate. The landscape features a mixture of manicured lawns and mature woodlands with walking trails.

Waterfront home w/ Beach access

At Après Sea you are surrounded by natural beauty - Scorton Creek on the back of the house & East Sandwich Beach across the street from the front of the house. You'll love quiet walks on the beach, Cape Cod bay, and the sunrises & sunsets. The house is perfect for entertaining with an open air deck, covered deck, natural gas BBQ, chef's kitchen, and 5 TVs. Parking for up to 6 cars. Welcoming World Cup 2026 supporters!

Greycliff: Mohonk Preserve Getaway

Welcome to Greycliff! Enjoy unobstructed, panoramic views of the Shawangunk range from this newly reconstructed four bedroom home on five private acres. Inspired by our art glass collection, Greycliff has live, work, play space for up to 8 guests in exquisite surroundings in the heart of the Mohonk Preserve and in the shadow of its dramatic ridge. Featured in Hudson Valley Magazine!