Resort vacation rentals in Massachusetts

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Top-rated resorts in Massachusetts

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Resort in Hancock

4.54 out of 5 average rating, 72 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.

Oct. 11 – 18

$191 CAD per night

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.

Dec. 5 – 12

$721 CAD per night

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.

Jun. 22 – 29

$644 CAD per night

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.

Aug. 5 – 12

$478 CAD per night

Resort in Falmouth

Captain's Quarters charming oceanfront resort

Located across the street from Falmouth Heights Beach overlooking Vineyard Sound, this is the perfect spot for your escape to Cape Cod. It features a large outdoor pool and suites with a whirlpool tub. Each of the bright and classic suites at the Captain's Quarters is furnished with a fireplace, balcony, and a Jacuzzi tub. Guests can prepare meals with the kitchenette, complete with a 2-burner stovetop, full-size refrigerator, and microwave. Enjoy ocean view from you balcony!

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.

Dec. 27 – Jan. 3

$1,149 CAD per night

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!

Dec. 27 – Jan. 3

$242 CAD per night

Superhost

Hotel room in Wellfleet

4.87 out of 5 average rating, 38 reviews

The Motel at Even'tide Resort - 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.

Jul. 19 – 26

$479 CAD per night

Resort in Brewster

4.52 out of 5 average rating, 46 reviews

Ocean Edge Resort One Bedroom Condo

One Bedroom Condo at The Villages at Ocean Edge Resort. Condo offers separate bedroom with queen bed, living room with pull out sleep sofa, full kitchen, all linens, one bathroom and private patio or balcony. Daily housekeeping is provided. Guests have access to all property amenities.

Oct. 14 – 21

$442 CAD per night

Superhost

Hotel room in Wellfleet

4.77 out of 5 average rating, 13 reviews

The Motel at Even'tide Resort - Two Double Beds

Recently refurbished with new furniture, flat screen TV, refrigerator, and coffee maker. These rooms are very popular with guests looking for easy first floor access in a one story building. These comfortable rooms with two double beds are our most economical family accommodations.

Oct. 5 – 12

$303 CAD per night