950 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Barns
Boats
Bungalows
Cabins
Condos
Cottages
Estates
Farmhouses
Hotels
Homes
Lodges
Studios
Townhomes
Villas
Yachts
Castles
Chalets

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Massachusetts Downtown Vacation Rentals(950)

950 Results
$300 - $429
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
1 - 7 night minimum stay
(14)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
(72)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(56)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 4 night minimum stay
(14)
$245 - $345
per night
2 - 3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 3 night minimum stay
(9)
$215 - $457
per night
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
(13)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
(6)
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
1 - 7 night minimum stay
(11)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
(14)
$250 - $300
per night
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
(37)
$285 - $400
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
3 - 7 night minimum stay
(17)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 - 7 night minimum stay
(8)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(19)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
(15)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 night minimum stay
(8)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
(15)
$200 - $350
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(3)
$4,000 - $5,800
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
7 night minimum stay
(3)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(8)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 night minimum stay
(17)
$5,000
per week
7 night minimum stay
  • 5 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 9
7 night minimum stay
(5)
$414 - $1,414
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 12
3 - 7 night minimum stay
(16)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 - 7 night minimum stay
(5)
  • 5 BR,
  • 3 BA,
  • Sleeps 14
1 - 7 night minimum stay
(6)
$2,895 - $6,895
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 12
7 night minimum stay
$400 - $600
per night
1 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
(14)
$425 - $585
per night
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
(14)
$4,200
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$750 - $1,000
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(11)
 

Recent Massachusetts Reviews

Great condo, great owners!

5 of 5
Along with our two sons (aged 11 and 14), we visited Boston for a week and stayed at this property. I have had my share of short term rentals, and this by far has been the best experience, ever. Location/Neigborhood: The property is very close to Cambridge, Harvard Square (walked a few times, 20-30 mins max), has an on-street parking permit. Great neighborhood with small cafes and shops within walking distance. We left the lights on in our rental car one night, and a helpful neighbor (hi Bruce!) helped us jump it, and we met the other next door neighbor during the process (hi Adele!). Two grocery stores nearby, Whole Foods and Trader Joe's. Lots of kids in the neighborhood, everyone taking walks, running, going to the nearby park... Inside: VERY clean! Spotless! Tastefully decorated with everything labeled, and fully functional. Great taste, in my opinion, and has everything you might need. Plenty of hangers, great linens and mattresses, different types of pillows etc. Full kitchen with pots pans coffee grinder, coffee machine, teapots! Anything and everything you would need. Great entertainment system with plenty of movies and comfy couches with blankets! Feels totally home! Lots of books around, and cute decorative items such as typewriters (my kids were mesmerized). The washer and dryer work great, so pack light and do a load while there :) Owners: SO, SO sweet, attentive, lovely lovely people! Answered every email extremely quickly with all kinds of details, suggestions... Great coffee, great company, and an awesome baby! Can't wait to stay there again.
  • Submitted: Jan 11, 2015
  • Stayed: Nov 2014

Comfortable Oasis in a Perfect Location!

5 of 5
My daughter and son-in-law live in another state. However, a few years ago, they did live in Beacon Hill. They have always had a great fondness for the area so my husband and I treated them to a few days stay at this Condo after the Christmas Holiday. From the beginning, the Owner was so responsive and helpful. Her correspondance to us was complete and timely! It was a pleasure to work with her! My daughter and her husband were thrilled with the Condo and especially the Wonderful location! They had a Great time in the City, much of it due to the fact that they had this Cozy Condo to call "home" for a few days!The only problem is that from now on when they come to Boston, they will probably want Only to stay at this Comfortable Condo and not with family!!
  • Submitted: Jan 1, 2015
  • Stayed: Dec 2014

Perfect weekend getaway!

5 of 5
We stayed at Four Winds for a weekend wedding with some friends and had the most marvelous time. Mary Kay was a gracious host starting with the ease of booking to occasional check-ins and tips for places to go and see in Rockport. The 2-bed was in great shape and the location was ideal for views of the water and browsing of small boutiques, restaurants and shops. Mary Kay's gift shop downstairs had lots of selection and my wife and I purchased a few watercolors that we proudly display in our home. We couldn't have been happier with our choice and we'd gladly stay here again should we venture back to Rockport!
  • Submitted: Dec 30, 2014
  • Stayed: Oct 2014