A calm lake surrounded by dense forest with autumn foliage.

Holiday Homes in Medway

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Medway holiday homes

A spacious living area with a large sectional sofa, a glass coffee table, and a view of the outdoors through large windows.

1. 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, (7 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 €245
includes taxes & fees
1 Nov - 2 Nov
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
A living room with a glass coffee table, two sofas, a dining table with chairs, and lamps.

2. 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, (3 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 €650
includes taxes & fees
28 Oct - 29 Oct
4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
Private kitchen

3. 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, (7 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 €1,189
includes taxes & fees
6 Nov - 7 Nov
Game Day Hub < 1 Mi to Stadium & Patriot Place!
A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

4. 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 €400
includes taxes & fees
25 Oct - 26 Oct
Modern Upper-Level Oasis, Minutes to Boston.
A spacious living room with wooden beams, a sliding glass door to a patio, and a cozy seating area with a sofa and chairs.

5. 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.
Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with two chairs.

6. 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 €688
includes taxes & fees
15 Nov - 16 Nov
Bright & Cozy Woodland Home Near Foxborough
A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

7. 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 €489
includes taxes & fees
25 Oct - 26 Oct
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

8. 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 €350
includes taxes & fees
22 Oct - 23 Oct
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

9. 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 €357
includes taxes & fees
26 Oct - 27 Oct
totally remodeled house with fitness room, close to Boston and Worcester
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

10. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.6 out of 10, Excellent, (7 reviews)
The price is €474
includes taxes & fees
22 Oct - 23 Oct
Clifford Luxury Retreat 3BR Self Check In Home
A modern kitchen with white cabinets, stainless steel appliances, and wooden shelves. There is a dining area with wicker chairs and a wooden table.

11. Budget-Friendly Basement 2BR Retreat

Budget-Friendly Basement 2BR Retreat
Roslindale
10.0 out of 10, Exceptional, (21 reviews)
"What a beautiful hide-a-way! Truly a diamond in the rough. "
United States
Twanna M.
Budget-Friendly Basement 2BR Retreat
A modern bedroom with a wooden wall, a bed with grey bedding, a bedside table, a TV mounted on the wall, and a ceiling light.

12. Private Suite w/ Bath & Free Parking

Private Suite w/ Bath & Free Parking
Brockton
10.0 out of 10, Exceptional, (5 reviews)
"It was a very nice little place with a convienient patio deck."
United States
Robin
The price is €154
includes taxes & fees
4 Nov - 5 Nov
Private Suite w/ Bath & Free Parking
A modern office space with a desk, chair, and a flat-screen monitor.

13. Newly Renovated 3BR Private Home in Newton

Newly Renovated 3BR Private Home in Newton
Newton Center
The price is €328
includes taxes & fees
3 Nov - 4 Nov
Newly Renovated 3BR Private Home in Newton
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

14. Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A covered deck with outdoor furniture, a grill, and a sliding glass door leading to a bedroom.

15. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
United States
Laura P.
The price is €238
includes taxes & fees
22 Oct - 23 Oct
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
A modern kitchen with white cabinetry, a large island, and pendant lighting.

16. Luxury Home - Fire Pit - Beach Grill - 2 Decks

Luxury Home - Fire Pit - Beach Grill - 2 Decks
Smithfield
10.0 out of 10, Exceptional, (21 reviews)
"Very nice property. Great host. We left an air mattress as our appreciation. Thank you"
United States
cynthia P.
Luxury Home - Fire Pit - Beach Grill - 2 Decks
A living room with leather sofas, a coffee table, and a fireplace.

17. Luxury & Private 6BR Single House • Summer Retreat w/ Parking & Pet-Friendly 35

Luxury & Private 6BR Single House • Summer Retreat w/ Parking & Pet-Friendly 35
Randolph
10.0 out of 10, Exceptional, (5 reviews)
"I enjoyed the place it was clean and big."
United States
Princess K.
The price is €564
includes taxes & fees
26 Oct - 27 Oct
Luxury & Private 6BR Single House • Summer Retreat w/ Parking & Pet-Friendly 35
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a glass table and leather sofas.

18. Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2

Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
Dorchester
8.0 out of 10, Very good, (2 reviews)
"Was clean and easy to get into. Good amount of parking and easy to contact host with questions!"
United States
Julie C.
The price is €406
includes taxes & fees
25 Oct - 26 Oct
Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
A stainless steel range hood with a digital display and a warning label.

19. Designer Condo in Jamaica Plain | Steps to Forest Hills

Designer Condo in Jamaica Plain | Steps to Forest Hills
Roslindale
Designer Condo in Jamaica Plain | Steps to Forest Hills
A spacious living area with a dining table set for six, a sofa, and a kitchen in the background.

20. Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17

Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
Randolph
10.0 out of 10, Exceptional, (7 reviews)
"Great stay! Host was very responsive to any questions. Family friendly house with lots of beds and a wide open living room. Easy check in and check out process. Nice central location to all that the Boston area has to offer."
United States
Anonymous traveller
The price is €549
includes taxes & fees
3 Nov - 4 Nov
Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
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

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

10/10 Excellent
"Clean room and staff were helpful."
Lisa 3-night trip
Posted 1 hour ago
Four Points by Sheraton Boston Newton

Find out more about Medway

Medway Holiday Homes information

Number of reviews
157
Accommodation
232 Holiday Homes
Lowest Price
€154
Highest Price
€1,189