Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartment
Barn
Bungalow
Cabin
Chalet
Condo
Cottage
Estate
Farmhouse
Hotel
House
Lodge
Studio
Townhome
Yacht
Boat
Castle
Villa

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Massachusetts Ski Vacation Rentals(681)

681 Results
2 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
(28)
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
(49)
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
(13)
4 night minimum stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
(9)
$700 - $860
per night
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 11
(6)
3 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
(12)
2 - 7 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 16
(8)
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
(8)
4 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
(9)
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
(3)
3 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
(3)
3 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
(10)
2 night minimum stay
  • 6 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 16
(22)
1 - 2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 6
(6)
7 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
(13)
7 night minimum stay
  • 4 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 8
1 Review
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 16
(4)
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
$3,600 - $15,000
per month
30 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 night minimum stay
  • 6 BR,
  • 4 BA,
  • Sleeps 18
1 Review
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 17
(6)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 14
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
(15)
2 - 5 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 15
(9)
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
(17)
$350 - $500
per night
3 - 4 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(5)
2 - 3 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 10
(5)
 

Recent Massachusetts Reviews

Wonderful experience!

5 of 5
I have known Louis since the mid 90's and this is the first time I have stayed in his lovely home. The house was exceptionally clean and very comfortable. I stayed in the bird room where the linens were so comfy and decor was very homy. The kitchen was so well stocked I was in awe. I didn't get a chance to take advantage of that because Louis prepare breakfast for me every morning (sorry you won't have that luxury). The flower arrangements around the apartment were a great touch and the one before you enter the house was stunning. The first night we sat on the back porch with a glass of wine and watched the birds in the back yard. You would never know that you weren't in the country, so peaceful and relaxing. I have decided to paint the beautiful red cardinal that was flying about. The T is very close to Diamond House and a great way to get around the city for sightseeing and eating out. I highly recommend the Gardner Museum for anyone interested. Next time I would definitely plan on lunch at the museum. I returned to Georgia August 21, and am telling all my friends and clients that if they visit Boston they defiantly need to consider staying at Diamond House. Thanks Louis for making my first trip home in nine years one of the best vacations I have ever had. A great friend and host. Susan
  • Submitted: Aug 24, 2014
  • Stayed: Aug 2014

a relaxing stay

5 of 5
Our family enjoyed a lovely stay at your home. All was as promised. Accurate listing description and amenities. Clean and well- maintained. Very good customer service, and we would recommend this property. We enjoyed a variety of restaurants, concerts, movies etc. The house is also a "destination" house for relaxing.
  • Submitted: Aug 20, 2014
  • Stayed: Aug 2014

A True Gem with Impeccable Attention to Detail

4 of 5
This year marked our second year staying in this beautiful home. We stayed here for a week last year and increased it to two weeks this year as we loved our time there so much. As expected, our stay here again this year was wonderful. This home is all that you want a beach home to be and then some. You have central A/C should you need it, a fireplace, a stunning professional grade stove/oven and so much more, the list could go on. You feel as though you are not walking into someone’s rental house they spend little energy on but into someone’s home they so lovingly care for. It is open and airy with impeccable interior design and attention to detail. Nancy, the homeowner, goes above and beyond to ensure you have everything you need during your stay. The home is spotless upon arrival. Every amenity you could need is provided, functioning, and spotless clean for your use. The beach is literally steps away. My favorite part of this house are the large windows in the master bedroom that overlook the stunning view of the ocean. It is truly stunning to wake up to this view each day and to sleep with the windows open hearing the ocean waves. It is the perfect size for our family that includes my husband and two children (including a toddler). We also had relatives stay with us. Everyone had their own space, plenty of bathrooms, showers and you never had the feeling that you were cramped…. Which often happens when staying in the classic ‘beach home.” All you need is yourself and your bathing suit, your true ‘New England’ beach vacation is right here.
  • Submitted: Aug 19, 2014
  • Stayed: Jun 2014