List your Property
Winter Hill, Somerville, Massachusetts, United States of America

Winter Hill vacation rentals

We found 26 vacation rentals — enter your dates for availability

Discover a selection of 26 vacation rentals in Winter Hill, Somerville that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $32 per night, and houses and condos are popular options for a stay in Winter Hill. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency

Find the best place to stay — Winter Hill

Large, Convenient and Well Located 4 Bedroom near Assembly Row.

Sleeps 9 · 4 Bedrooms · 1 Bathroom
$167 avg/night
(4)

Top floor of one family home

Sleeps 4 · 2 Bedrooms · 1 Bathroom
$225 avg/night
(7)

Convenient and cozy 2 bedroom near Assembly Row-3rd Floor

Sleeps 5 · 2 Bedrooms · 1 Bathroom
$119 avg/night
(3)

Convenient Large 3 Bedroom near Assembly Row-Private Parking

Sleeps 7 · 3 Bedrooms · 1 Bathroom
$179 avg/night
(1)

3RD Floor unit · Sun-Drenched, Quiet 3rd Floor,3 bedrooms

Sleeps 6 · 3 Bedrooms · 1 Bathroom
$165 avg/night
(9)

Sunny, Renovated 4 Bdrm, 2 Bath Apt in Somerville w/Parking and Outdoor Space

Sleeps 6 · 4 Bedrooms · 2 Bathrooms
$135 avg/night

Search 26 vacation rentals

Top rated rentals — Winter Hill
Stayed Dec 2020

Just what we needed

This lovely, comfortable apartment was just what we needed. The well-stocked kitchen allowed us to do all our own cooking, and there are plenty of amenities within walking and driving distance - as well as outdoor spaces where we could safely visit w...

Lynne Doherty H.
Lynne Doherty H.
Stayed Dec 2020

Wonderful location, excellent communication

My two sons and I traveled to Boston to visit my son and his wife who is doing doctoral research for Harvard. The apartment had everything we needed for a comfortable stay. It’s very convenient to downtown Boston and other suburbs. Salem and Plymouth...

Terri A.
Terri A.

Folsom, California

Stayed Dec 2019

Easy accommodation

Great localization. Well equipped house. Points to know: Coffeemaker is Keurig; bring your own pod. There will be $20 charge if you choose to park in the driveway. The details of the house- keys and times- won't be available until the day before your...

Maya B.
Maya B.

Enfield

Stayed Oct 2019

Great for a large party or event!!

Great location for a younger crowd and large parties! Bar downstairs is awesome but can be loud - bring ear plugs if you want to sleep prior to 1/2am. Owners are great and very responsive and super personable! Had everything we needed there - great f...

Sheri C.
Sheri C.
Stayed Sep 2019

This place is perfect!

We stayed in this apartment. It's so cute! Very clean. The neighborhood was super quiet. There was off street parking!!! We arrived a little earlier than expected and we were allowed to enter early, which was awesome! The host left a thank you note, ...

Denise F.
Denise F.
Stayed Sep 2019

Light and bright newly renovated

The kitchen and living areas were nice and bright! Communication with Seamus was awesome always getting right back to us! Great little deck to enjoy happy hour. Nice having dual controls for air and heat so upstairs bedroom can control their own temp...

Debbie Q.
Debbie Q.
Stayed Sep 2019

Comfortable, Cozy and Clean

Lovely hosts in a quiet, pretty area of town made our whirlwind trip to Boston a huge success. Each bedroom has its own heat and a/c and the bathroom boasts a Rainforest showerhead! One morning I took a relaxing walk in the neighborhood. A great way ...

Suzanne D.
Suzanne D.
Stayed Aug 2019

Cozy Boston Hideaway for 2

My daughter and I stayed here while I helped her move back in to Northeastern about 5 miles away. Claudia and Jim's small lower level flat was perfect for us as a home-base to get to and from campus quickly. Also, nicely within walking distance of So...

Garrett H.
Garrett H.
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

How many vacation rentals are available around Winter Hill, Somerville?

Our 2021 property listings offer a large selection of 26 vacation rentals around Winter Hill. From 11 house rentals to 15 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Winter Hill?

Yes, of course. Vrbo has 11 Houses in Winter Hill. Our other popular types of vacation rentals in Winter Hill include:

  • Condos/Apartments: 15 rentals available
  • Studios: 12 rentals available
  • House: 11 rentals available

Can I find a vacation rental with pool in Winter Hill?

Yes, you can select your preferred vacation rental with pool among our 2 vacation rentals with pool available in Winter Hill. Please use our search bar to access the selection of vacation rentals available.