Resort holiday rentals in Massachusetts

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Top-rated resort rentals in Massachusetts

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Superhost

Resort in Hancock

4.62 out of 5 average rating, 68 reviews

Country Village 3 Bedroom 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

4.55 out of 5 average rating, 73 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.

Resort in Dennis

4.6 out of 5 average rating, 5 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

4.67 out of 5 average rating, 3 reviews

Beachside Cape Cod Resort

Situated on the beautiful sandy beaches of Nantucket Sound is The Breakers Resort, one of two Bluegreen Vacations resorts in Dennis Port, MA. Comfortable one-bedroom unit welcome you to relax and unwind in this cozy beachside community. Take in the beauty of our private sparkling beach then head out for a fun-filled day. At the resort fire up the grill and BBQ for the family. The kids will appreciate the playground nearby and everyone can make a splash in the on site outdoor heated pools.

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.

Resort in Chatham

5.0 out of 5 average rating, 5 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.

Resort in Barnstable

5.0 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.

Resort 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!

Superhost

Hotel room in Wellfleet

4.87 out of 5 average rating, 38 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.