Holiday rentals in Simmons Pond

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Top-rated holiday rentals in Simmons Pond

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Top guest favourite
The exterior of the historic schoolhouse displays white siding and a gabled roof. Two prominent front doors, labeled 'No 1,' provide entry. The bell tower features a visible bell, and the surrounding landscape includes carefully arranged flower beds and a stone path.
Farm stay in Tiverton
4.95 out of 5 average rating, 249 reviews

4 Corners Schoolhouse No.1 Kristin &Sakonnet Farm

Stay at the renovated Old Tiverton Four Corners Schoolhouse No. 1, a historic gem built in 1800. The exterior mirrors its original schoolhouse facade, while the interior blends modern comforts with historic charm. The home features a gourmet kitchen, cozy living room with a wood-burning fireplace, two bedrooms, and a Whirlpool tub. Located within walking distance of Tiverton Four Corners village, offering unique shops, restaurants, and more. No pets allowed. Ask for your free weekend itinerary!

Top guest favourite
A hot tub is situated under a shaded gazebo, surrounded by lush greenery and blooming hydrangeas. The area is well-maintained with neatly trimmed grass and subtle outdoor lighting, creating a serene space for relaxation.
Home in Middletown
4.98 out of 5 average rating, 102 reviews

Coastal Hideaway- hot tub close to Newport+beaches

Welcome to The Coastal Hideaway! Just off Indian Avenue within walking distance of Pebble Beach, your friends or family can relax by lounging on the outdoor patio, rocking on the side porch, or soaking in the hot tub. You can also enjoy the local beaches, visit Sweet Berry Farm, taste the local cuisine, and enjoy the many artisan shops in downtown Newport (just 15 minutes away). Brand new listing, this home is well equipped with everything from beach chairs to a pack-n-play to a chef's kitchen.

Top guest favourite
An outdoor dining area overlooks the tranquil cove. The table is surrounded by six wicker chairs, set against a backdrop of calm blue water and a clear sky dotted with fluffy white clouds.
Cottage in Portsmouth
4.97 out of 5 average rating, 150 reviews

Waterfront Oasis minutes from Newport w/ hot tub!

Welcome to our charming waterfront Oasis! Located on Blue Bill Cove, our private cottage is steps away from Island Park beach, dining, & local attractions. Stroll down Park Ave to enjoy some ice cream and burgers at Schultzy's or a lobster roll from Flo's Clam Shack (seasonal) while you take in the ocean views. Head to Bristol or Newport, relax at one of the local vineyards and breweries, or enjoy a day on the golf course. Our cottage is also conveniently located near wedding venues & colleges.

Guest favourite
A serene view of the Westport River at dusk features soft pastel hues reflecting on the water. A wooden dock extends into the calm river, framed by gentle grasses in the foreground. The sky transitions from deep blue to warm oranges and yellows as the sun sets.
Cabin in Westport
4.94 out of 5 average rating, 319 reviews

Koselig Cabin on the Farm Coast of New England!

This cabin is full of comforts, convenience, and love. Just miles from Horseneck Beach. It is located under a mile to Buzzards Bay Brewery and Westport Rivers Winery and a 5 minute walk to the quiet little neighborhoods private beach on the East Branch of the Westport River. Koselig embodies feelings of family, friends, warmth, love, coziness, contentment, and comfort. We have a custom area and house guide at the Cabin with everything you need to know to maximize your experience in the area!

Guest favourite
A charming entrance to a tiny house is bordered by vibrant flowers and greenery. Two blue chairs provide a seating area by the door, complemented by potted plants. The wooden deck appears inviting and well-maintained, enhancing access to the home.
Tiny home in Middletown
4.99 out of 5 average rating, 161 reviews

Cozy coastal tiny house getaway

Situated on Easton's Point, brand new ocean front tiny house looks across to Mansion Row with access to a rocky beach for lounging, swimming, or fishing. The property is close to downtown Newport & ideally located between three beaches. The cozy unit has a queen bed, full bath & kitchenette with coffee maker, fridge, and toaster oven. There is a small deck with ocean views, access to ocean front, outdoor shower and off street parking. We provide beach chairs, a beach umbrella and towels.

Guest favourite
A sprawling green lawn extends towards Nanaquaket Pond, framed by lush trees and shrubs. The calm water reflects the sky, dotted with clouds, while distant homes can be seen along the shoreline. A sandy area is visible, inviting exploration.
Home in Tiverton
4.98 out of 5 average rating, 168 reviews

Coastal Charm!

**3/12/26 Booking calendar reopened for spring and summer! Registration # RE.00841-STR Coastal charm! This waterfront property has expansive views of Nanaquaket Pond, a salt water inlet and a private walking path down to the shoreline! Bring your kayaks or paddle board if you like. Explore the farm coast, beaches, nature preserves, historic areas and much more! The perfect getaway to relax in, catch a gorgeous sunset from the back deck and take a walk down to the shoreline.

Top guest favourite
A quaint cottage is blanketed in snow, with a chimney rising from the sloped roof. Nearby, a bare tree stands, its branches weighed down by frost. The scene conveys a tranquil winter landscape, featuring soft white tones and a serene atmosphere.
Tiny home in Westport
5 out of 5 average rating, 149 reviews

Restored blacksmith shop (cottage) on goat farm

Guest cottage on 300-yr old farmstead, now a working goat farm. Open floor plan with Queen bed, decorative FP, loveseat, ++ seating, bistro table/chairs, WiFi, Roku TV w/ prem. channels, a/c & heat, 3 cu. ft. frig, m'wave, coffee maker/tea kettle. NO KITCHEN facilities. Full bath (w/ shower) in attached ell. Bright & cheery, close to barn & goat pen. Shaded outdoor grass patio w/ teak furniture. Orchard (w/ fire pit), pastures, hay fields, stream, walking trails in woods.

Top guest favourite
A handcrafted tree house is perched among trees, supported by wooden stilts. The structure features a rustic exterior with a metal roof and large windows, surrounded by greenery and vibrant pink flowers in the foreground, creating a serene and natural setting.
Treehouse in Wareham
4.97 out of 5 average rating, 222 reviews

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

Top guest favourite
A charming cottage exterior is presented, featuring shingle siding and a welcoming wraparound deck. Outdoor seating includes a picnic table and several armchairs surrounded by planters with blooming flowers. Large windows provide ample natural light, enhancing the inviting atmosphere of the space.
Home in Little Compton
4.94 out of 5 average rating, 142 reviews

Salt box

Come and Relax! Newly renovated guest cottage in little Compton, Rhode Island on a quiet dead end street. Access to beach, close to town commons, farmers market and Sakonnet and Westport wineries among other special spots. Wonderful walking and biking area. Perfect for couples or a small family to get away. Special note...Memorial Day to Columbus Day house includes a beach pass to Briggs beach. More info will be shared as needed.

Top guest favourite
A serene outdoor path is lined with tall grasses and lush greenery, leading towards a one-story ranch-style home in the distance. A large tree provides shade, and the open meadow stretches out on either side, creating a peaceful and natural setting.
Home in Little Compton
5 out of 5 average rating, 15 reviews

Relaxed Dog Friendly Coastal Retreat

Escape to the charm of Little Compton at this private coastal retreat, perfect for a relaxing getaway. You’ll be staying in a cottagey one-story ranch-style home and barn set back from the road on four acres of wildflower meadow. Whether you’re looking to explore nearby beaches, stargaze from the hot tub, or enjoy a game night in the air-conditioned barn, this home offers a serene and comfortable stay. Perfect for pets as well!

Top guest favourite
Aerial view showcases a peaceful coastal neighborhood, with homes set against a backdrop of the ocean. The green lawns and sandy shore create a harmonious landscape. Soft clouds drift above, and the water glistens under natural light, enhancing the serene coastal environment.
Flat in Little Compton
4.96 out of 5 average rating, 344 reviews

Home by the Sea

Private entrance to the full 1st floor with an ocean view in quiet neighborhood. The apartment features a bedroom with full sized bed, private bathroom, private living room with dining area, gas fireplace, tv and couch. Washer/dryer, refrigerator, microwave, coffee maker, toaster and hot plate included are in the apartment. There also is an additional outdoor H/C shower, private patio and gas grill.

Top guest favourite
The exterior of a beach cottage is showcased, featuring a gravel driveway and a lush garden area. Large windows provide views of the calm water, while a covered porch offers a shaded entryway. Vibrant fall foliage frames the backdrop along the shoreline.
Cottage in Bristol
4.98 out of 5 average rating, 186 reviews

Beach Front Cottage in Bristol

“Sandy” “Clean water swimming” Beach front cottage in Historic Bristol, RI. This Cottage has a sandy beach front for family fun! Just minutes away from museums & restaurants. Centurally located between Newport, & Providence, RI (30-minute drive) You could not ask for a closer proximity to the beach front and scenic water views.

Popular amenities for Simmons Pond holiday rentals