Villa holiday rentals in Massachusetts

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Popular amenities for villa rentals in Massachusetts

Private villa rentals

Guest favourite
Villa in Stockbridge
4.93 out of 5 average rating, 46 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

SujayRating, 5 stars1 month ago
This was our second year staying at the house over President's Day weekend and it was just perfect, again. We have a big group -- 10 adults, 10 kids -- and we're able to make it work comfortably. It is a very welcoming and homey house - one that's clearly been a part of the family for a long time. There are a lot of bedrooms and lots of character. The kitchen is well stocked. The dining room can fit all of us. Honestly, we have nothing but positive things to say about it.
Superhost
Villa in Newton
4.67 out of 5 average rating, 46 reviews

Stays in May

GregRating, 5 stars4 months ago
Mark and his villa were perfect for us during our "displacement" for almost 2 weeks while our floor was redone. He was the perfect host: 1 - being beyond accommoative with our quick displacement 2 - was an excellent communicator and lightning quick responses before/during/after our stay 3 - the villa is in a gorgeous area, with plenty to do nearby and all the amentities you could want: grocery stores, restaurants, and things to see/do super close 4 - there's plenty of room throughout the house for everyone (including our dog!) 5 - the kitchen is well-stocked both with cooking staples and equipment, even had a fresh bag of coffee waiting for us! I can't recommend him and this listing enough, whether you are displaced during reno's like we were or just in the area and looking for a place that can feel like a home away from home. It has everything you could need/want from my perspective, and I am very picky when I am spending an elongated period of time. Thanks Mark, was a pleasure :)
Villa in Gloucester
4.6 out of 5 average rating, 5 reviews

Sunset Cove: Waterfront home in the Goose Cove

JasonRating, 5 stars20 months ago
The Cape Ann area was lovely for a family vacation. The house has tremendous views. Spacious and well-appointed. Great spot to soak in the water views. Very comfortable.
Superhost
Villa in South Lee
4.79 out of 5 average rating, 122 reviews

Villa with Access to Amazing Amenities!

PamelaRating, 5 stars5 months ago
The place was great and wish i had more time there. We were just looking for a quick overnight with two bedrooms, which this was, but it seemed like a lovely place for a vacation.
Top guest favourite
Villa in Cambridge
4.99 out of 5 average rating, 246 reviews

Phil's Harvard & MIT Home

LynnRating, 5 stars5 days ago
Phil's place was just lovely and the neighborhood was lovely. We would definitely stay here again. We were in Boston on a college tour and it was perfect for our family for our stay. It was really nice having waters provided -- thank you so much! And, the parking permit also came in very handy.
Superhost
Villa in Charlton
4.78 out of 5 average rating, 67 reviews

Winter Home near TreeHouse Brewery with King Beds

CaraRating, 5 stars5 months ago
We got married at a venue about 15 minutes away so we stayed here with our bridal party and the size was perfect. Everyone slept comfortably, we still had plenty of space. The neighborhood is quiet and the location is still close enough for us to enjoy exploring Sturbridge. Michael was responsive and honest with any question I asked!
Guest favourite
Villa in Plymouth
5 out of 5 average rating, 34 reviews

Ocean View Luxury Villa with Inground Pool

SandraRating, 5 stars7 months ago
Christina’s home is even more beautiful and spacious in person - the pictures do it no justice. Very clean home that provided everything we needed to make our stay feel like home (there was even a Dyson vacuum cleaner and swiffer - not all homes provide the best tools needed to tidy up during the stay but this one did!). The location was great - close to supermarket, restaurants, beaches etc. Plymouth is a beautiful town. Christina was one of the best hostesses I’ve ever had - you could tell a lot of thought was put into every detail of the home. She also responded right away to small issues we had here and there during our stay with much warmth and kindness. This is a must return to home for me! Thank you!
Superhost
Villa in South Lee
4.85 out of 5 average rating, 27 reviews

Spacious Villa with Access to Various Amenities!

EileenRating, 5 stars2 weeks ago
**Title: A Slice of Paradise at the Five-Star Serenity Resort** From the moment we arrived at the Five-Star Serenity Resort, we were enveloped in an atmosphere of luxury. **Accommodations:** Our suite was nothing short of spectacular. Spacious and elegantly designed, it featured breathtaking views, a private balcony, and a lavish bathroom complete with a soaking tub and rainfall shower. The attention to detail was impeccable, from the plush bedding to the locally sourced decor that added a unique touch to our experience.

Villa rentals with a pool

Guest favourite
Villa in Stockbridge
4.93 out of 5 average rating, 46 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

SujayRating, 5 stars1 month ago
This was our second year staying at the house over President's Day weekend and it was just perfect, again. We have a big group -- 10 adults, 10 kids -- and we're able to make it work comfortably. It is a very welcoming and homey house - one that's clearly been a part of the family for a long time. There are a lot of bedrooms and lots of character. The kitchen is well stocked. The dining room can fit all of us. Honestly, we have nothing but positive things to say about it.
Villa in Wareham
4.87 out of 5 average rating, 76 reviews

Perfect Summerhouse for Families- Golf/Pool/Beach

HeidiRating, 5 stars5 months ago
We had a wonderful stay and enjoyed this sprawling home in the center of a golf course. The host was friendly and responsive and the home had all the amenities we wanted. The yard was great for the dogs to run, and the beach and Audubon were within walking distance. Highly recommend.
Superhost
Villa in South Lee
4.79 out of 5 average rating, 122 reviews

Villa with Access to Amazing Amenities!

PamelaRating, 5 stars5 months ago
The place was great and wish i had more time there. We were just looking for a quick overnight with two bedrooms, which this was, but it seemed like a lovely place for a vacation.
Superhost
Villa in South Lee
4.68 out of 5 average rating, 34 reviews

Villa with Access to Various Amenities

KrystaRating, 5 stars9 months ago
Fantastic communication. Easy in and out. No complaints at all!
Top guest favourite
Villa in Longmeadow
5 out of 5 average rating, 51 reviews

Comfort and Luxury - 180 year Old Gothic Estate

EdRating, 5 stars4 months ago
Paul’s place had the style of grand old home but it didn’t feel old: everything worked as it should, the kitchen and baths were updated and gorgeous. Amazing. We visited with family over 3 days and it was a fantastic, comfortable place to be together. Paul was gracious and helpful. Furniture and beds were of high quality and comfy. The grand piano in the living room was an extraordinary instrument and very much in tune - it was played for hours. All the guests gushed about the place, several saying it felt like a classic movie set. Can’t say enough about how much we enjoyed it. We very highly recommend
Superhost
Villa in Charlton
4.78 out of 5 average rating, 67 reviews

Winter Home near TreeHouse Brewery with King Beds

CaraRating, 5 stars5 months ago
We got married at a venue about 15 minutes away so we stayed here with our bridal party and the size was perfect. Everyone slept comfortably, we still had plenty of space. The neighborhood is quiet and the location is still close enough for us to enjoy exploring Sturbridge. Michael was responsive and honest with any question I asked!
Guest favourite
Villa in Newton
4.94 out of 5 average rating, 64 reviews

Explore Boston in style! Dream home, pool, sauna.

MichaelRating, 5 stars2 months ago
Beautiful well appointed home with lots of space for sleeping, bathing, and common spaces for gathering. Beautiful modern kitchen with everything we needed for our seven person group. Comfortable beds and overall surroundings, beautifully decorated in great condition. We stayed in the winter so we did not get use of the pool or hot tub, even though I believe the hot tub was ready to jump right in, but it was 25° out with wind chills in the teens. The master bathroom suite was probably our favorite thing about the home, heated floors and towel bar with a soaker tub and multi outlet shower as well as a heated toilet seat with modern bidet features. Didn’t use the fireplace or the sauna, but the massage chairs were a hit. We will definitely stay here again!
Guest favourite
Villa in Plymouth
5 out of 5 average rating, 34 reviews

Ocean View Luxury Villa with Inground Pool

SandraRating, 5 stars7 months ago
Christina’s home is even more beautiful and spacious in person - the pictures do it no justice. Very clean home that provided everything we needed to make our stay feel like home (there was even a Dyson vacuum cleaner and swiffer - not all homes provide the best tools needed to tidy up during the stay but this one did!). The location was great - close to supermarket, restaurants, beaches etc. Plymouth is a beautiful town. Christina was one of the best hostesses I’ve ever had - you could tell a lot of thought was put into every detail of the home. She also responded right away to small issues we had here and there during our stay with much warmth and kindness. This is a must return to home for me! Thank you!

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