Holiday houses in Simmons Pond

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Top-rated holiday rentals in Simmons Pond

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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, 260 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 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
4.98 out of 5 average rating, 195 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 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
4.93 out of 5 average rating, 332 reviews

Koselig Cabin on the Farm Coast of New England!

This cabin is full of comforts, convenience, and love. Just 4 miles from the ocean. 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 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, 179 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.

Guest favourite
Two colorful kayaks are positioned on a concrete dock, with the calm waters of the bay extending into the distance. The sky above is clear with some soft clouds, reflecting a tranquil outdoor setting.
Cottage in Westport
4.89 out of 5 average rating, 132 reviews

Kayaks and Glimpses of Westport Bay

Stay in a lovely and comfortable cottage with partial views of the bay. The water is just a short walk away past our neighbor with shared access to the water. Enjoy swimming, fishing, or relaxing on the float and soak up the sun. You can also explore the Horseneck Beach, wander the trails, taste the local farms and restaurants, and more. If you want to unwind at the cottage, watch shows on the 65" Samsung Smart TV, fast Wi-Fi, sit on the deck, and flip some burgers on the gas grill.

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
5.0 out of 5 average rating, 162 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.

Guest favourite
The master bedroom features a spacious bed adorned with light blue bedding and decorative pillows. A mirrored wall decor adds elegance, while a tray with rolled towels and flowers sits at the foot of the bed. Two bedside lamps provide soft lighting.
Casa particular in Portsmouth
4.91 out of 5 average rating, 117 reviews

Summer Home Near *Newport Attractions*

Is a beautiful house in a quiet and relaxed area of ​​Portsmouth. with a pleasant fully enclosed outdoor space for you and your children to enjoy. Is close to everything, shops, restaurants, beaches, vineyards, farms, Golf, Polo Games and many more activities to do, In addition, David's House is only 15 minutes from historic Newport and its beautiful mansions , water sports, boat trips and all its spectacular nightlife if what you want is a getaway with your friends.

Top Guest favourite
Home in Little Compton
5.0 out of 5 average rating, 66 reviews

Sakonnet Bungalow by the Vineyard

Come and unwind at our cozy home away from home! Explore the charming town of Little Compton, visit its local coffee shops, greenhouses, and learn about its rich history at the town center. Then, stroll through the grass led pathway that leads you to Sakonnet Winery. Our property offers the perfect spot to relax in the front chairs and watch the breathtaking sunset over the cornfield. Bring your family and let our home be your sanctuary!

Guest favourite
Two wooden adirondack chairs are positioned on a grassy area, facing a tranquil lake surrounded by trees. Bright yellow daffodils bloom nearby, adding a touch of color to the natural landscape under a clear blue sky.
Guesthouse in Dartmouth
4.89 out of 5 average rating, 193 reviews

Lovely Lakeside Cottage

Keep it simple at this peaceful and centrally-located cottage. Lovely lakeside cottage with open floor plan. Centrally located in southeastern Massachusetts with short drives to Boston, Providence, Newport, and Cape Cod. Several beaches within 20 minutes. Washer/ Dryer on site and California King Size bed. A simple five (5) minute ride to UMass Dartmouth. Cottage has a living room, full kitchen, bedroom, full bath, and small dining area.

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
5.0 out of 5 average rating, 22 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.
Apartment in Little Compton
4.96 out of 5 average rating, 357 reviews

Home by the Sea free beach pass

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
A charming cottage, framed by lush green trees and a well-maintained lawn, stands under a clear blue sky. The exterior features a classic design with a light-colored facade and large windows, offering a glimpse of the sunroom. Surrounding landscaped areas provide a serene and welcoming environment.
Home in Little Compton
5.0 out of 5 average rating, 20 reviews

Period Cottage Minutes To Ocean

Period Cottage In Idyllic Country Setting, Minutes From Ocean; Pet-Friendly. Chaffee Cottage, circa 2006, was designed from an 18th-century cape and has all the modern-day amenities, such as central air, washer/dryer, dishwasher, outdoor shower, high-speed wireless internet and cable HDTV. Various beaches are nearby in both RI and MA. Access to the Westport River is available in Adamsville.

Popular amenities for Simmons Pond holiday rentals