Vacation rentals in Western Connecticut Planning Region

Newly built twin beach house within steps to beach

Keep it simple at this peaceful and centrally-located home. Newly built in 2019! Premier beach living at its finest. Steps to Fairfield’s beaches and less than a mile to downtown restaurants, shops, and bars. Fenced backyard. Central air throughout. Decks off the front and back with a Weber grill. Furnished with luxury furniture, sheets, comforters, and pillows. Smart TVs in every bedroom and living room. Tesla charging station at the house. Identical home next door available for larger bookings

The Lakeside Nook

Enjoy all that Candlewood Lake and Squantz Pond State Park have to offer in the comfort of our home. Come reconnect with love ones and relax in the serene surroundings. Located close to the lake, the home features 3 bedrooms, 2 full baths, plenty of indoor and outdoor entertaining space, 2 fireplaces (gas and wood burning stove) and large table for family meals. Toiletries and all linens are included and we have paddle boards available for guest use . Please read house rules before booking.

Secluded Lakefront Chalet-Firepit&yard Dogfriendly

Take it easy at this unique & tranquil getaway just over 1 hour from Nyc. 200 feet of private lake front all yours to enjoy. Secluded, modern chalet & fireplace. King size bed. Spacious bedroom & bathroom. Farm style dining table, sofa & daybed in open concept living room. Desk & lounge area with record player, karaoke & TV. Large sun room with comfy daybed & gorgeous lake views. Lakefront dining & swing. Fenced yard, deck,fire pit,bbq. Lots to do nearby! We❤️dogs. Serenity awaits!

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Private Hilltop Cabin at Houndcliffe

Start your next adventure and step into Houndcliffe, just 90 min from NYC and 10 min from downtown. Our picturesque 3-bedroom cabin on top of a rolling hill, will greet you with incredible views from in the house or elevated porch. Recently renovated mountain retreat is the quintessential outdoor getaway, central to many of Litchfield County's restaurants, shopping, and adventures. Perfect for family fun, couples retreats, visits to local farms, and other activities for up to 10 guests!

Modern + Spacious 5BR/2BA Home, Renovated Backyard

✨ Modern Renovated 5BR/2BA Home in Ideal Location ✨ Stay in style and comfort at this newly renovated 5-bedroom, 2-bathroom home, just steps from the best dining, shopping, and attractions. 💡 Why You’ll Love It: • Fully Equipped Kitchen 🍳 – Cook like a chef! • Luxury Bedding 🛏️ – Rest easy with premium linens. • Spacious Living Areas 🛋️ – Perfect spaces to unwind. • Stunning Backyard 🌳 – Relax and entertain in style. Book now for an unforgettable stay!

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.