Resort holiday rentals in Massachusetts

Find and book unique resort rentals on Airbnb

Top-rated resort rentals in Massachusetts

Guests agree: these resort rentals are highly rated for location, cleanliness and more.

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Private room in Hancock

4.62 out of 5 average rating, 95 reviews

Club Wyndham Bentley Brook - Two Bedroom Suite

Club Wyndham Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this resort an exceptional choice for mountainside play. Ski or snowboard down the well-groomed trails of Jiminy Peak, enjoy hiking, tennis and mountain biking, or swimming at the on-site pools. This suite offers a king bed in the master bedroom, two full beds in the guest bedroom and a sleeper sofa in the living room. Additional amenities include a kitchen and dining area, washer/dryer and a balcony.

Private room 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.

Resort in Dennis

4.75 out of 5 average rating, 4 reviews

Beachfront 1 BR Suite, Dennis Port July 12 - 19

Located at the beach, a cozy one bedroom fully furnished suite on and overlooking Nantucket Sound, unit 211 is on the second floor, first level containing full bath, living - dining room combination, kitchenette with full-sized refrigerator, microwave, coffee maker, fireplace and enclosed deck containing the hot tub. On the second level is the master bedroom (king bed) with balcony overlooking The Sound. Beautiful private beach, heated pool and BBQ area. Unfortunately, no pets.

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Private room in Chatham

4.88 out of 5 average rating, 8 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.

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Private room in Yarmouth

5 out of 5 average rating, 6 reviews

August 8-15.Riverview Resort! Two baths. 6 people

Second week in August.King-size bed with full bath ensuite with sofa bed; THEN, in living room, another sleeper sofa and half bath, large refrigerator/freezer. Free parking, 2TVs, cable, wifi, AC. First level with sliding doors to beautiful courtyard overlooking Parker River with BBQ grills. On-site washer/dryer next to communitykitchen,exercise,game room. Near beaches. Across from Captain Parker’s Restaurant and Pirates Cove putt-putt. Indoor pool; hot tub;gym.

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Private room in Chatham

5 out of 5 average rating, 16 reviews

Pleasant Bay Village Resort - Extra Deluxe Queen

All accommodations at Pleasant Bay Village Resort are located in small single story buildings accessed from the gardens. The Extra Deluxe Rooms with two Queen beds are our largest hotel style rooms set in a quiet, peaceful section of the property with a short walk to the pool & hot tub. 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.

Private room in Barnstable

5 out of 5 average rating, 7 reviews

Luxury 3 Bed Apartment in Hyannis with Waterpark

We are renting out some of our weeks at the Cape Codder Resort. It is a full hotel, and the unit is a 3 Bedroom apartment located inside the hotel. The place is great because you have your own private space. They just upgraded the wireless so it is quite good. You are minutes away from the beaches and center of Hynannis. You can find out more about the Residence Club and the Cape Codder Resort by going to their website.

Private room in Pittsfield

Charming 1 Bedroom - 4 Star Resort w/ pool

Located 1/2 mile from Lenox the Berkshire Mountain Lodge is a destination for all seasons: Everything you want to explore is right outside the door. Nearby you’ll find a bevy of activities for outdoor enthusiasts, farm-to-table dining and many opportunities to enjoy the arts; Tanglewood, Hancock Shaker Museum, MASS MoCa, Williams College of Art Museum and the Clark!

Private room in Fairhaven

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.

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Hotel room in Wellfleet

4.84 out of 5 average rating, 45 reviews

The Even'tide - One Queen Bed

Contemporary rooms with one queen bed, refrigerator, coffee maker, and flat screen TV. Designed and decorated with your comfort in mind. Our most economical room for two. Sorry, children and babies are not permitted in these rooms. They are welcome in our family suites, cottages, and rooms with two double beds.