A calm lake surrounded by dense forest with autumn foliage.

Medway Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Medway vacation rentals

A dining area with a round table, yellow chairs, a potted plant, and a Buddha painting on the wall.

1. Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Hopkinton
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
The price is ￥22,613
￥33,554 total
includes taxes & fees
Oct 20 - Oct 21
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
A spacious living area with a large sectional sofa, a glass coffee table, and a view of the outdoors through large windows.

2. Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Westwood
10.0 out of 10, Exceptional, (6 reviews)
"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."
United States
Eva O.
The price is ￥31,604
￥45,892 total
includes taxes & fees
Nov 14 - Nov 15
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

3. Modern Upper-Level Oasis, Minutes to Boston.

Modern Upper-Level Oasis, Minutes to Boston.
Norwood
9.8 out of 10, Exceptional, (9 reviews)
"Cute, welcoming, and everything we needed. Host was very responsive and we had a blast."
United States
Travis B.
The price is ￥30,577
￥68,396 total
includes taxes & fees
Oct 19 - Oct 20
Modern Upper-Level Oasis, Minutes to Boston.
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

4. Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (10 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is ￥22,597
￥37,773 total
includes taxes & fees
Nov 10 - Nov 11
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A modern hotel lobby with a seating area, a bar, and a kitchen.

5. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (258 reviews)
"Wonderful!!"
United States
Huynh
The price is ￥16,704
￥18,658 total
includes taxes & fees
Nov 1 - Nov 2
Residences at Solomon Pond
A living room with a sofa, a coffee table, a TV, and a hallway leading to other rooms.

6. Private Luxury 2 Bedroom Suite

Private Luxury 2 Bedroom Suite
Framingham
8.0 out of 10, Very good, (13 reviews)
"Overall we had a great time"
United States
David W.
The price is ￥18,765
￥24,492 total
includes taxes & fees
Oct 28 - Oct 29
Private Luxury 2 Bedroom Suite
A living room with a glass coffee table, two sofas, a dining table with chairs, and lamps.

7. 4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking

4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
Norwood
10.0 out of 10, Exceptional, (2 reviews)
"Not only was Joseph, our host, very accommodating, but the house was amazing! Each bed was comfortable, and each room had a TV. The life size connect 4, the video games, and the fact that every room had AC was an exciting surprise. I would definitely recommend staying here."
United States
Chris B.
The price is ￥51,910
￥115,701 total
includes taxes & fees
Oct 28 - Oct 29
4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
A spacious room with large windows, a wooden dining table with chairs, and a view of the outdoors.

8. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely place to stay! This site was meticulously clean, gardens and decor both zen and whimsical, trails well maintained, near a grocery and other shopping. I will stay again!"
United States
Melanie S.
The price is ￥33,895
￥40,742 total
includes taxes & fees
Nov 16 - Nov 17
Zen Inspired Retreat with Private Forest Trails
A modern kitchen with stainless steel appliances, wooden ceiling, and a dining area with a wooden table and chairs.

9. Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
Lincoln
10.0 out of 10, Exceptional, (33 reviews)
"Everything was clean and welcoming. Kitchen had everything you need to cook, make coffee, etc. charming and comfortable "
United States
Lindsey D.
The price is ￥18,804
￥34,587 total
includes taxes & fees
Oct 25 - Oct 26
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

10. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,317 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is ￥20,909
￥23,356 total
includes taxes & fees
Nov 6 - Nov 7
Crescent Suites Hotel
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

11. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.6 out of 10, Exceptional, (33 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is ￥32,426
￥55,811 total
includes taxes & fees
Oct 29 - Oct 30
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Private kitchen

12. Game Day Hub < 1 Mi to Stadium & Patriot Place!

Game Day Hub < 1 Mi to Stadium & Patriot Place!
Foxborough
10.0 out of 10, Exceptional, (6 reviews)
"Our host was amazing. We had an excellent time visitng family and part of this was due to our accommodations. The host made sure we had even had wood for the fireplace outside."
United States
mark
The price is ￥103,819
￥211,456 total
includes taxes & fees
Oct 19 - Oct 20
Game Day Hub < 1 Mi to Stadium & Patriot Place!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with two chairs.

13. Bright & Cozy Woodland Home Near Foxborough

Bright & Cozy Woodland Home Near Foxborough
Foxborough
9.2 out of 10, Wonderful, (9 reviews)
"Great host hospitality"
United States
Elijah S.
The price is ￥76,520
￥96,953 total
includes taxes & fees
Oct 21 - Oct 22
Bright & Cozy Woodland Home Near Foxborough
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

14. totally remodeled house with fitness room, close to Boston and Worcester

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.2 out of 10, Wonderful, (17 reviews)
"Nicely located in neighbor with easy access to highways and walking distance to coffee shop this single home is perfect for being near Boston. Space is comfortable with all the comforts of home. "
United States
Karyn V.
The price is ￥31,446
￥55,070 total
includes taxes & fees
Nov 8 - Nov 9
totally remodeled house with fitness room, close to Boston and Worcester
A spacious living room with wooden beams, a sliding glass door to a patio, and a cozy seating area with a sofa and chairs.

15. Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!

Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
Framingham
10.0 out of 10, Exceptional, (3 reviews)
"Clean, pet friendly"
United States
Rebecca M.
The price is ￥55,465
￥119,673 total
includes taxes & fees
Oct 20 - Oct 21
Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

16. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"The house was nice. The beds were very comfortable. The house was close to everything. Check-in and check-out process was easy."
United States
Christina S.
The price is ￥43,803
￥79,111 total
includes taxes & fees
Oct 18 - Oct 19
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Interior

17. Gillette Soccer Event HQ < 1 Mi to Patriot Place!

Gillette Soccer Event HQ < 1 Mi to Patriot Place!
3.0 star property
Foxborough
The price is ￥120,411
￥206,834 total
includes taxes & fees
Oct 19 - Oct 20
Gillette Soccer Event HQ < 1 Mi to Patriot Place!
A gazebo with a stone barbecue grill and a table with chairs.

18. Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.0 out of 10, Wonderful, (71 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
The price is ￥21,807
￥36,715 total
includes taxes & fees
Oct 28 - Oct 29
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Room

19. Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Dedham
9.2 out of 10, Wonderful, (16 reviews)
"Great place for nearby Boston and driving around."
United States
Justin
The price is ￥21,333
￥42,185 total
includes taxes & fees
Oct 18 - Oct 19
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
A two-story house with a gabled roof, multiple windows, and a front porch.

20. Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.6 out of 10, Exceptional, (32 reviews)
"We were very pleased with the cleanliness, size of the 2 bedrooms, the kitchenette, bathroom and location! Our Host was very easily contacted and responded quickly always --- we would highly recommend this location as it was easy access to major highways. Will definitely stay again when another function happens! TY Delphine!"
United States
Patricia B.
The price is ￥28,286
￥36,184 total
includes taxes & fees
Oct 27 - Oct 28
Charming 2-bedroom apartment with WiFi, AC in superb Canton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Medway Hotel Reviews

Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham

10/10 Excellent
"Good breakfast, but no hot tub"
James 2-night trip
Posted 1 hour ago
Embassy Suites by Hilton Boston Waltham

Find out more about Medway

Search for holiday rentals in Medway on Expedia! You can easily find your home rentals, villas, holiday apartments in Medway using one of the methods below:

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Look no further and take a look at our great range of rental properties in Medway!

Frequently asked questions

Are there vacation rentals in Medway?

Yes, we offer vacation rentals near top attractions in Medway, or you can go with a secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Medway?

Boston's Best Vacation Home : This vacation home rental outside of Medway is equipped with a fireplace, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

What’s there to see and do in Medway?

Explore the area and cultural attractions such as Gillette Stadium, or visit a family-friendly sight such as Supercharged Entertainment. Charles River and Regal Bellingham are a couple of places you'll find in the larger area.

What’s a vacation rental in Medway like?

A vacation rental is a private property you can stay in for short or long periods in Medway. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family gatherings.