Vacation rentals in Simmons Pond

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Top-rated vacation rentals in Simmons Pond

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Guest favorite

The historic home showcases a charming exterior with weathered shingle siding and multiple large windows. A small ornamental tree is planted in the front garden, surrounded by well-maintained flowerbeds with colorful blooms. A stone marker displays the address '513' prominently.

Place to stay in Westport

4.9 out of 5 average rating, 118 reviews

Coastal Retreat with Historical Charm

Planning a visit to Southern New England? The historic home is centrally located near Newport, Providence, Cape Cod and the ferry to Nantucket. Westport is a charming seaside community with a relaxed and peaceful atmosphere. You will enjoy private accommodation in a historic home designed for a luxurious stay. Surrounded by a kaleidoscope of art and design, treat yourself to a king-sized Posturepedic bed enveloped in pressed linen sheets, sumptuous bath, heated floors and walk in rain shower

Superhost

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, 298 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!

Top guest favorite

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, 135 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 favorite

A spacious loft area is highlighted by angled skylights, providing natural light. A cozy queen-sized sleigh bed is situated against the wall, accompanied by a dresser. Two rocking chairs are placed on an area rug, creating a welcoming seating space. Cabinets line the opposite wall.

Loft in Little Compton

4.92 out of 5 average rating, 75 reviews

The Nest at Willow Farm

It’s the best of both worlds. Work online with blazing fast internet. Rest and recharge in a serene farming community. Dogs are most welcome! Enjoy Little Compton’s famous golden afternoon light. Explore Lloyds Beach, the Town Commons, Adamsville Village, and the trails at Wilbur Woods. Walk your dog in the safety of the 10 acre tree farm behind my home. Little Compton is a unique place forgotten by time, and is home to the largest collection of historic fieldstone walls in New England.

Top guest favorite

A small guesthouse is set against a clear blue sky, surrounded by lush green grass and blooming wildflowers. Trees and vegetation add to the natural scenery, while the house features multiple windows that offer a glimpse of the interior.

Guesthouse in Westport

5 out of 5 average rating, 12 reviews

The Swift's Nest

Visiting the Farm Coast? Why not stay on a Farm! The Swift's Nest is a guest house located on our working farm and garden. The studio apartment is private and accessed by a farm lane that will take you past our apiary, orchard and wildflower gardens. Located above our honey room, this generous studio enjoys exceptional views. Distant winter views of the Westport River are replaced by a bright pastoral of wildflowers, hayfields, and forests in the summer. Come enjoy and relax.

Top guest favorite

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, 130 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 favorite

The exterior of the home is showcased, featuring a two-story structure with shingle siding and multiple windows. A large, green lawn extends in front of the house, complemented by a red-leaf maple tree. The surrounding landscape is filled with greenery, creating an inviting outdoor space.

Home in Little Compton

4.94 out of 5 average rating, 103 reviews

Brimstone Hill Farm, Little Compton, RI

Our home is close to the town center, beaches, restaurants, local farm stands and winery. You’ll love our place because of the two cozy bedrooms upstairs & large living room downstairs. There is no kitchen, but we have an outdoor grill and private terrace at your disposal. Our large, beautiful property is good for couples, solo adventurers, and families (with kids). We are flexible when it comes to check-in and offer the use of our in-ground pool as part of your package.

Guest favorite

A charming farmhouse is set against a backdrop of autumn foliage, featuring vibrant trees and a cloudy sky. A garden with various plants and flowers is visible in the foreground, adding natural texture to the scene.

Loft in Westport

4.88 out of 5 average rating, 291 reviews

Brithaven Farm

Brithaven Farm is on 28 acres of fields, woods meadows and gardens. We are just 2 miles from East Beach and the Allen's Pond Wildlife Sanctuary. We are completely private from the road and reached by a long laneway through woods which opens up to fields and meadows The rental has 2 decks, one with a large awning with dining table and chairs to lounge and take in the view. There is an open plan living, dining kitchen area with french doors leading to the deck.

Guest favorite

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, 136 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 favorite

An open interior view showcases a welcoming living space featuring a kitchenette with light wood cabinetry and a refrigerator. A cozy seating area is visible, complete with a loveseat and armchair. Natural light streams through multiple windows, enhancing the warm atmosphere.

Apartment in Tiverton

4.95 out of 5 average rating, 158 reviews

NEAT, somewhat funky STUDIO APARTMENT - WATERVIEW

Apartment has a queen bed, 2 chairs, dresser, small loveseat, TV (with Fire Stick for streaming); kitchenette with refrigerator, coffee maker, oven/broiler, microwave, blender, utensils, cookware; bathroom. There is a private entrance plus a slider out to the patio (yours during your visit), with our expansive gardens. You'll be left a small continental breakfast, coffee/tea, as well as some of our veggie harvest when available..

Top guest favorite

A private deck is shown, featuring a glass-topped table surrounded by six metal-framed chairs. Potted flowers add a touch of color, while trees provide natural shade and greenery. The clear blue sky enhances the serene atmosphere of the outdoor space.

Home in Little Compton

4.88 out of 5 average rating, 125 reviews

John Dyer Loft by Kristin & Sakonnet Farm & Stays

Enjoy privacy in this charming second-floor space near Adamsville. It features a queen bedroom, comfy living room, full kitchen, two smart TVs, and central A/C and heat. Relax on the private deck with views of woods and a historic cemetery. The home includes a washer/dryer, and a portable crib is available upon request. Close to beaches, vineyards, and breweries. No pets allowed. Winter monthly rate does not include utilities.

Top guest favorite

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, 330 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.