Resort vacation rentals in Massachusetts

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Top-rated resort rentals in Massachusetts

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Superhost
A seating area features a comfortable grey sofa and a plaid armchair, facing a flat-screen TV mounted on the wall. A stone fireplace is located beneath a wooden mantel, with decorative items displayed above. Natural light brightens the space through a nearby window.
Resort in Hancock
4.67 out of 5 average rating, 95 reviews

3 Bedrm 1/2 mile off base at Jiminy Peak- No fees!

This is a 3 bedroom business listing for Jiminy Peak located in Country Village condo area about a 1/4-1/2 mile off the base of the mountain. All units are all privately owned and we are the management company that rents these units in the owners interest. The pictures you see are a collection of our different units that we rent. The floor plan of each condo is the same, it will just be different décor and furnishings. If you want something specific you will need to call the property directly.

Resort in Hancock
New place to stay

Slope view ski-in/out 1br condo hotel @Jiminy Peak

Ski-In/Ski-Out Cozy Escape Imagine waking up on the top floor of a slope-view condo-hotel, sipping coffee while gazing out at pristine mountain runs. This spacious 1-bedroom retreat comfortably sleeps 4. Why Guests Love It ski-in/ski-out access: Step outside and you’re on the slopes. Slope Views: Watch skiers carve down the mountain. Night Skiing: Extend the fun after sunset with illuminated trails. Resort Amenities: Swim in the year-round outdoor heated pool or soak in the in/outdoor jacuzzis.

Guest favorite
The spacious room includes two queen beds dressed in coordinating linens. A marble dining table is set with a fresh fruit arrangement, and yellow accents are present with two large cushions. A comfortable armchair and desk offer additional seating and workspace.
Resort in Chatham
4.9 out of 5 average rating, 20 reviews

Pleasant Bay Village Resort Rear Deluxe Studio

Pleasant Bay Village Resort’s Rear Deluxe Studios can be booked directly with the property or here on Airbnb and feature two queen beds, a fully equipped kitchen and dining area. The room offers a private deck overlooking the Koi pond. Pets are allowed in the Rear Deluxe Studio only at a rate of $25 per pet per night. We are a family friendly Hotel, NO PARTIES only peaceful enjoyment while respecting all guests and neighbors. Rate is based on 2 people, $20/night for each additional person.

The image showcases a serene shoreline with gentle waves lapping against the sandy beach. In the background, several oceanfront buildings are visible, set against a clear blue sky. The proximity of the buildings to the water highlights the coastal setting.
Resort in Dennis
4.5 out of 5 average rating, 6 reviews

Ocean front 2-bedroom suite on beautiful beach

Two bedrooms, jacuzzi tub, ocean view out the windows, nice sandy beach, grill, kitchen, outdoor pool. You must book for an entire week at a time (Friday to Friday). Please read all descriptions and carefully review the photos with their captions. This is NOT a beach house. It is the closest to the ocean 2-bedroom suite in the resort's oceanfront building with views across the dunes to the ocean. The pool is down the stairs outside the door; the pool itself is directly above the beach.

The room features two double beds with crisp linens and a simple layout. A work desk with a chair and a lamp offers a functional workspace. Glass French doors lead to a bluestone patio, providing views of the surrounding gardens.
Resort in Chatham
4.91 out of 5 average rating, 11 reviews

Pleasant Bay Village Resort - Standard Room

The Standard Rooms at Pleasant Bay Village Resort in Chatham, Cape Cod can be booked directly with the property or here on Airbnb and feature two double (full size) beds, updated bathrooms and a glass door leading to a tranquil bluestone patio with a small table and two chairs, overlooking beautiful gardens. We are a family friendly Hotel, NO PARTIES, only peaceful enjoyment respecting all guests and neighbors. Rate is based on 2 people, $20/night for each additional person.

Guest favorite
The Great Room features comfortable, neutral-toned seating arranged around a circular wooden table. A large HD TV is mounted above a gas fireplace, while a large Palladium window allows natural light to fill the space, complemented by soft drapes.
Resort in Barnstable
5 out of 5 average rating, 9 reviews

Luxury 3 Bed Apartment in Hyannis with Waterpark

We are renting out some of our weeks for our 3 Bedroom apartment in Hyannis, MA. It is located at the Margaritaville Resort. You will have your own private space where you can be comfortable in your apartment while having access to the amenities at the resort. The entire property has just undergone a renovation. You will be minutes away from the beaches and center of Hyannis. You can find out more about the property at by searching for "Margaritaville Hyannis".

Superhost
The exterior of a three-story resort building features a stone façade, multiple balconies, and well-maintained landscaping. A brick fence and pathway are visible in front, providing access from the road. The sky appears cloudy, suggesting an overcast atmosphere.
Resort in Falmouth

Captain's Quarters, Cape Cod

AVAILABLE JULY 11-18, 2025 Captain's Quarters in Falmouth Heights, is one of the few resorts to have the Ocean across the street. From the balcony you can enjoy the sunset, relax in the Jacuzzi, or enjoy the night life that is within walking distance. The Martha's Vineyard ferry is about 1/2 mile from the resort. Shopping, restaurants, and movie theater are close by. This unit is on the second floor and has two bedrooms, 2 baths. Kitchenette and living room.

Superhost
A living room area features a comfortable gray sofa facing a television on a wooden stand. A small coffee table sits in front of the sofa, and a patterned area rug covers the dark wood floor. Natural light enters through a window with wooden blinds.
Resort in Hancock
4.79 out of 5 average rating, 43 reviews

2 Bedrm 1/2 mile off base at Jiminy Peak- No fees!

These are our 2 bedroom business listings for Jiminy Peak located in our Country Village and Mountainside condo area about a 1/4-1/2 mile off the base of the mountain. All units are all privately owned and we are the management company that rents these units in the owners interest. The pictures you see are a collection of our different units that we rent. If you want something specific you will need to call the property directly.

A cozy sitting area contains a navy sofa and a round wooden table. A decorative piece featuring an oceanic motif adorns the wall. Soft light emanates from a lamp beside the sofa, while vibrant blue orchids and a welcoming sign contribute to the room's charm.
Hotel room in Wellfleet
4.84 out of 5 average rating, 19 reviews

The Even'tide - One Bedroom Suite

Spacious bedroom with two queen beds, TV, refrigerator, microwave and coffee maker. Cozy front sitting room with table and chairs, sofa bed and second TV. A door separates the two rooms. Both families with children and couples with different sleep schedules or TV viewing habits enjoy the flexibility that two TVs and a separate sitting room provide. Daily maid service provided.

The bathroom features a modern design with a mosaic tile accent wall. A white pedestal sink and a toilet are positioned against the wall. A bathtub with a shower curtain is visible in the background, and a large mirror reflects the space.
Resort in Fairhaven
4.67 out of 5 average rating, 3 reviews

Modern Deluxe Studio with Waterfront Views

In our deluxe studio you will have the ultimate luxurious hotel experience. The deluxe studio features a huge King Size Bedroom with flat screen television as well as an alarm clock radio, plenty of storage, spacious living area with a deluxe sofa, coffee table, and 55″ flat screen television. Each deluxe studio features a newly renovated bathroom.

Superhost
The living area features a comfortable seating arrangement with two red armchairs and a dark blue sofa. A round wooden coffee table is centered, complemented by a glass dining table with chairs nearby. Natural light is offered through large windows, adorned with soft drapes.
Resort in Yarmouth

The Cove 1 week 9/12-9/19/25

The Cove at Yarmouth in West Yarmouth, Massachusetts (Cape Cod). This is a timeshare resort and is full of amenities. Conveniently located in the heart of Cape Cod. One week only for 2025, Check in 9/12/25 check out 9/19/25 (Friday to Friday). For 2026 and 2027 dates will be in June (6/5/26-6/12/26, 6/4/27-6/11/27)

A cozy bedroom features a spacious bed with white linens, positioned near three windows that allow natural light to fill the room. Soft cream walls and light-colored furnishings enhance the welcoming atmosphere, while bedside lamps provide additional illumination.
Resort in Brewster
4.31 out of 5 average rating, 87 reviews

Ocean Edge Resort One Bedroom Villa

Stay directly with Ocean Edge Resort for full access to resort amenities! One Bedroom Villa includes daily housekeeping, all linens, private bedroom with queen bed, sleep sofa in living room, full kitchen, one bathroom, washer/dryer private balcony or patio.

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