
Holiday rentals in Sterling
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Top-rated holiday rentals in Sterling
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"Mystic Country" Farm Stay at 100 Acre Wood
Let us welcome you to 100 Acre Wood, a historic farm and working cattle ranch. Owl's House is a private and stylish guest house nestled within the trees and garden and offers 180° views. Our farm store is stocked with our own TX Longhorn beef and pasture-raised chicken and eggs, plus curated with local products. Enjoy pastoral farm life and our private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

"Amanita" Tiny Cabin on Beach Pond Shore w/Sauna
Reconnect with nature at this unforgettable escape with amazing lake views. Welcome to our newest addition! "Amanita" takes tiny and cute to a whole new level. At just 8' x 12' this tiny space has everything you need for a relaxing lakefront getaway. Wake up to stunning views of crystal clear Beach Pond just steps from the cabin. Take an early morning swim or paddle in one of our kayaks. Then sooth sore muscles in our wood-fired traditional Finnish Sauna. Then enjoy an evening lakeside campfire.

Come relax at Lakeside Landing
Come relax and enjoy lakefront living in this 2 bedroom, 1 bath house on Boone Lake. 1st BR offers a king size bed and 2nd BR offers a twin over full bunk bed with a trundle. Enjoy open concept living with beautiful views of the lake. Inside you will find wifi, streaming on 3 tvs, Wii, board games, puzzles and books. Relax on the large deck, enjoy yard games or use the 2 kayaks, canoe or paddle board. A perfect place for a relaxing family getaway. Ring camera at front door only for security.

Brookside Chalet
Not just a place to stay but a place where you will want to stay. - Dedicated parking space - Well-appointed full kitchen - Deck overlooking Mashamoquet Brook (our guests refer to it as the tree house:) The bed will be the highlight of your experience. This high quality queen is accessorized with a pillow top mattress, goose down and memory foam pillows and spa quality sheets and pillow cases. Location: - Five minute drive to Pomfret Prep. - Ten minute drive to main Street in Putnam.

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.

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly
Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

Artist studio in the woods
Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quiet, tranquil, relax. 47 minutes from Gillette Stadium.

Historic Hearthstone Cottage
Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

Beautiful Studio - < 15 mins 2 downtown & Brown
Relax, work, and unwind in “The Treehouse,” our serene, light-filled studio apartment nestled among the trees. Perfectly located in historic Rumford, RI, it’s just 3 miles from Brown, RISD, and Johnson & Wales, and 5 miles from Providence College. Enjoy quick access to the East Side of Providence, Newport, and Little Compton beaches. Conveniently close to Amtrak, bus lines, and the airport, it’s an ideal spot for exploring New England or visiting area colleges.

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.

Stay in Decadence | One-of-a-Kind Flat on Broadway
A magazine-worthy flat inside a Gothic Victorian mansion on Providence's West End. Guests call it "one of the best Airbnbs ever"- and it shows. Spotless, beautifully designed, steps from Federal Hill's best restaurants, and directly across from The Nitro Bar. Dedicated off-street parking included. Perfect for a weekend getaway, a romantic escape, or a work trip with everything you need at your door.

2 Bd Apt- 20 min to Foxwoods/25 min to Mohegan Sun
Very new, clean and quiet 1000 sqft 2 bedroom apartment. The apartment is located over an office and is 20 minutes from Foxwoods and 25 minutes to Mohegan Sun. You’ll have the whole apartment to yourself with access to central AC, thermostat controls heat, WiFi and laundry - much better than staying in a hotel! Bedroom 1: Queen sized mattress Bedroom 2: Queen sized pull out sofa.
Popular amenities for Sterling holiday rentals
Other great holiday rentals in Sterling

Historic Railroad Caboose - Unique CT Farm Escape

Historic Haskell House 1700s Get Away!

Wildflower Cottage at Bittersweet Farm

Backyard Tiny House in the Woods

"The Getaway" at Alexanders Lake

The Fairy House - As Seen on HGTV!

Little Rest Studio

Lakeside Landing
Destinations to explore
- Gillette Stadium
- Mohegan Sun
- Foxwoods Resort Casino
- Six Flags New England
- East Matunuck State Beach
- Ocean Beach Park
- Charlestown Beach
- Bonnet Shores Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Point Judith Lighthouse
- Easton Beach
- Roger Williams Park Zoo
- Narragansett Town Beach
- University of Connecticut
- The Breakers
- Second Beach
- University of Rhode Island
- Soundview Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Ocean Beach
- Horseneck Beach
- Easton's Beach





