Resort holiday rentals in Massachusetts

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.

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.

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.

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.

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.

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".

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.

Surfside Studio March 20 - 27, 2026 2-7 days

March 20 - 27, 2026 Enjoy a fabulous Cape Cod experience when you stay at this special place. A full kitchenette, TV, full bathroom , queen bed and a pull out sofa for extra guests. It's right across from the private beach to enjoy the shore. If it's raining outside , enjoy the pool inside! When you return to your studio, grab some pool towels and take a jump in the indoor pool and hot tub. Walk to restaurants and scenic shoreline.

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.

The Cove 1 week 6/5/26-6/12/26

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 2026, Check in 6/5/26 check out 6/12/26 (Friday to Friday). For 2026 and 2027 dates will be in June (6/5/26-6/12/26, 6/4/27-6/11/27)

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.

King Room with Harborview

Newly renovated comfortable standard room features a king size bed, and a 50 inch flat screen television. You can enjoy in room amenities like fridge, microwave, alarm clock with radio, large desk area, and controlled air temperature for your ultimate relaxation.