Holiday rentals in Sterling

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Top-rated holiday rentals in Sterling

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A serene view of the home surrounded by lush greenery and blooming trees, reflected in the calm waters of the nearby pond. The property is framed by tall trees, creating a peaceful atmosphere in the rural setting.

Home in Hopkinton

Estate with lake near beaches & Westerly

Let this be your home away from home. Large, open, & upscale, with a cozy mix of comfort & nostalgia. Enjoy time with family & friends in our spacious, welcoming home on 40 acres, surrounded by fields, orchards, woods, stone walls, & lake with canoe, kayaks & paddle boards. Great for family vacations, reunions, retreats, & celebrations. Weddings welcome - contact owner for details. Pet friendly. Close to beaches, Watch Hill, Foxwoods. 5 min to I-95. 35 min to Providence airport. 4 night min.

LocationValueQuiet

4.89 out of 5 average rating, 142 reviews

Guest favourite

A serene view of Johnson’s Pond is presented, featuring calm waters reflecting the surrounding trees and homes. A grassy area leads to a wooden dock, providing private water access. Steps descend towards the water, inviting relaxation by the peaceful shoreline.

Home in Coventry

Awesome 3 bed vacation lake house. Great location!

Three bedroom house right on Johnson’s Pond with private water access right in the back yard. House features queen master with deck overlooking the pond. 2nd bedroom features a full bed with twin bunk bed above along with a stand alone twin bed. 3rd bedroom has a queen bed. Perfect for one or two couples to share. Full kitchen and laundry along with WiFi and streaming services. Use of 2 kayaks and pedal boat. Just two miles from I-95, so everything in southern New England is just minutes away!!

LocationValueComfort

4.88 out of 5 average rating, 163 reviews

Top guest favourite

The exterior of a bright red caboose is captured against a backdrop of tall trees. Sunlight filters through branches, highlighting the unique structure. A pathway of gravel leads to the entrance, which features steps and a small platform. The inviting colors complement the natural surroundings.

Guest house in Brooklyn

Historic Railroad Caboose - Unique CT Farm Escape

🚂 Authentic 1906 SOO-Line Caboose on our working CT horse farm! Queen Murphy bed + two bunks, WiFi, Roku, microwave, fridge, Keurig, deck, and cozy bathroom. Note: The historic 22" doorways limit accessibility. Explore nearby: Mashamoquet Brook trails, antique shops, wineries, and Putnam's arts district. Farm life starts early! Fall asleep to railroad dreams, wake to countryside serenity. Note: historic charm means cozy dimensions. Book today—before this experience leaves the station! 🌿

FamilyValueAir conditioning

5.0 out of 5 average rating, 91 reviews

Superhost

An outdoor deck features a spacious dining set with an umbrella, surrounded by a lush lawn. A comfortable seating area with sofas is visible, all set against a serene lake backdrop. The atmosphere is complemented by green hedges and clear skies.

Home in Coventry

Spacious Lakehouse w/ Private Beach

Our house is equipped to make your stay comfortable and filled with activities for all ages! - We have a total of four bedrooms, which includes 5 beds; 3 king sized beds, and 2 queen sized beds - Two full bathrooms with showers - 5 kayaks & 1 canoe with 3 seats - Stone firepit for bonfires and night gatherings - Large new TREX deck with sofas and outdoor dining set - String lights from the lake to the back porch - Large 65" TV & FREE WIFI - Washer & dryer - Restaurants & amenities RE 05846 STR

LocationValueCheck-in

4.88 out of 5 average rating, 78 reviews

Top guest favourite

A camp cottage exterior is shown, featuring a wooden facade with a red trim. Two rocking chairs are situated on the porch, inviting relaxation. Multiple windows allow natural light to enter, and a pathway leads to the entrance among the surrounding trees.

Cabin in Voluntown

Ellis -Lakeside Cabin on Beach Pond with Sauna

Year round quintessential lakeside vacation! Ellis is a fully heated/winterized camp cottage just steps from beautiful Beach Pond. It has two bedrooms and sleeps 5. The detached bunkhouse has 3 single beds and is available for larger groups (summer only) Very peaceful lakeside location just 238 feet from Beach Pond. Walking distance to trails. Visit our 6 horses. Not a secluded space so make sure to look at the photos to see the layout of other nearby buildings. Please read all the details!

ValueLocationHiking

4.95 out of 5 average rating, 752 reviews

Top guest favourite

The spacious main living area features wooden floors and high ceilings. Sunlight floods in through large windows, illuminating a comfortable sectional sofa and a dining table with white chairs. An open kitchen is visible in the background, enhancing the airy feel of the space.

Barn in Brooklyn

The Barn at Pondview

Reconnect with nature at this unforgettable escape. Enjoy pond views and incredible sunsets from the top patio deck. This property is on the 2nd & 3rd floors of the barn, so there are stairs. Also the "bedroom area" picture is a loft area with a trundle bed, (2 twin beds) - the room is open to the downstairs main living area. The game room has pool, shuffle and foosball tables, darts and a bar area. There is also a basketball court in the back yard. Inground pool in the summer.

LocationFamilyPets

5.0 out of 5 average rating, 56 reviews

Top guest favourite

Tiny home in Mansfield

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

LocationCheck-inComfort

5.0 out of 5 average rating, 41 reviews

Top guest favourite

Home in Voluntown

Cozy, quiet country getaway near Mystic, casinos

Rest and recharge on 48 secluded acres in the quiet countryside. The home is remodeled with modern amenities. Enjoy hooting owls as you gaze at a million stars in the night sky. Area offers family fun activities, hiking trails, fishing. 30 minute or less drive to: • Mystic CT: Seaport, Aquarium, Holiday gift stores • Stonington Borough (CT)-quaint shops • Live music; 7 wineries; brew pubs • Foxwoods, Mohegan Sun 35 min. to Providence RI (Airport; Zoo) 45 min. to historic Newport RI

ValueLocationBeach

4.94 out of 5 average rating, 50 reviews

Top guest favourite

A two-story house is framed by lush greenery and vibrant flowering shrubs. The exterior showcases a combination of brick and wood, with multiple windows allowing natural light to fill the interior. A clear blue sky with scattered clouds completes the picturesque setting.

Home in Exeter

Nature's Nook

Beautifully decorated 4-bedroom, 2.5 bath house with views of nature from every window. This airy modern house on 5-acres offers: privacy, fire pits, picnic tables, a swimming pool, volleyball/badminton, basketball and giant outdoor Jenga games. Open floor plan for socializing & board games, with TV, internet & movies. Nearby hiking trails, large lake, & ski area. Wake up to the chatter of birds, breakfast on the deck and escape the constant noise & distractions of daily life.

LocationValueNearby

4.91 out of 5 average rating, 154 reviews

Top guest favourite

An open living space showcases a blue sectional sofa facing large glass doors offering views of the lake. A high-top kitchen island with sleek marble countertops is visible, along with bar stools. Natural light fills the area, enhancing the welcoming ambiance.

Home in Preston

Lake House w/Game Rm 5 Min From Foxwoods & Mohegan

Relax and enjoy the breathtaking views of this new contemporary lakefront home. Kayaks & paddleboards await you, 5 min from Foxwoods, 10 min from Mohegan Sun with multiple-choices of hiking, boating, shopping and dining. Stunning cathedral, ceilings, fully equipped kitchen, with granite countertops, tiled showers with full amenities and a game room/theater. You cannot get any closer to the water. This two bedroom 2 1/2 bath sleeps eight, 2200 square-foot house completed in 2024.

LocationValueComfort

5.0 out of 5 average rating, 103 reviews

Top guest favourite

Home in Griswold

Waterfront Home | Newly Renovated | Chef's Kitchen

Wake up to a private pond. Step onto your deck and the water is right there. This cottage is a newly renovated (2026) waterfront home on Aspinook Pond in Jewett City, CT. Two bedrooms plus a pull out couch, a chef-outfitted kitchen built to actually cook in, and a breathtaking master bathroom. Two kayaks, a canoe and a skiff, a public boat launch, and a fully stocked pond ideal for fishing. Dogs welcome. Self check-in. Foxwoods + Mohegan Sun Casino: 20 min.

FamilyLocationAccuracy

5.0 out of 5 average rating, 30 reviews

Top guest favourite

A modern kitchen features white cabinetry and granite countertops, equipped with a refrigerator, microwave, and stove. A small dining table is set with white chairs, and a potted plant adds a fresh touch. Natural light enters through a nearby window.

Guest suite in Brooklyn

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

LocationValueCheck-in

4.94 out of 5 average rating, 242 reviews