Vacation rentals near Wine & Cheese Cask
We found 3,052 vacation rentals — enter your dates for availability
Select the perfect vacation home within close proximity to Wine & Cheese Cask. Vacation rentals offer the best amenities for your stay with friends, family, or just your pet, like cable TV and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Wine & Cheese Cask
Showing deals for:Nov 7 - Nov 14
Image gallery for Exquisite North End 1brm
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Exquisite North End 1brm
Boston, MA
5% off
Price is CA $346
CA $346
CA $3,257 total
CA $3,257 total
includes taxes & fees
Image gallery for Perfect North End Studio
9.49.4 out of 10 rating
Exceptional
(31 reviews)
Perfect North End Studio
Boston, MA
5% off
Price is CA $303
CA $303
CA $2,864 total
CA $2,864 total
includes taxes & fees
Image gallery for Beautiful Boston Brownstone!
1010 out of 10 rating
Exceptional
(76 reviews)
Beautiful Boston Brownstone!
Boston, MA
10% off
Price is CA $620
CA $620
CA $5,689 total
CA $5,689 total
includes taxes & fees
Image gallery for 80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
9.49.4 out of 10 rating
Exceptional
(15 reviews)
80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
Boston, MA
10% off
Price is CA $406
CA $406
CA $3,844 total
CA $3,844 total
includes taxes & fees
Image gallery for Central Boston Beacon Hill 2brm
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Central Boston Beacon Hill 2brm
Boston, MA
5% off
Price is CA $464
CA $464
CA $4,328 total
CA $4,328 total
includes taxes & fees
Image gallery for NEW 2BR Historic Marblehead Home+Minutes to Beach
1010 out of 10 rating
Exceptional
(9 reviews)
NEW 2BR Historic Marblehead Home+Minutes to Beach
Marblehead, MA
10% off
Price is CA $347
CA $347
CA $3,259 total
CA $3,259 total
includes taxes & fees
Image gallery for Spacious vacation townhome unit with a pool
1010 out of 10 rating
Exceptional
(12 reviews)
Spacious vacation townhome unit with a pool
Weston, MA
10% off
Price is CA $420
CA $420
CA $3,631 total
CA $3,631 total
includes taxes & fees
Image gallery for Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!
Beverly, MA
10% off
Price is CA $406
CA $406
CA $3,694 total
CA $3,694 total
includes taxes & fees
Image gallery for Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
1010 out of 10 rating
Exceptional
(65 reviews)
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Boston, MA
10% off
Price is CA $1,835
CA $1,835
CA $16,185 total
CA $16,185 total
includes taxes & fees
Image gallery for Modern 2BR/ Close to Boston with a lovely outdoor space
9.49.4 out of 10 rating
Exceptional
(22 reviews)
Modern 2BR/ Close to Boston with a lovely outdoor space
Melrose, MA
10% off
Price is CA $309
CA $309
CA $2,905 total
CA $2,905 total
includes taxes & fees
Image gallery for West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
9.89.8 out of 10 rating
Exceptional
(62 reviews)
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Boston, MA
19% off
Price is CA $391
CA $391
CA $3,793 total
CA $3,793 total
includes taxes & fees
Image gallery for Spacious Fully Loaded Retreat near forest, sea & easy access to Boston
1010 out of 10 rating
Exceptional
(5 reviews)
Spacious Fully Loaded Retreat near forest, sea & easy access to Boston
Cohasset, MA
10% off
Price is CA $620
CA $620
CA $5,472 total
CA $5,472 total
includes taxes & fees
Image gallery for Back-Bay Upscale Central Penthouse W Roof-top
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Back-Bay Upscale Central Penthouse W Roof-top
Boston, Massachusetts
20% off
Price is CA $634
CA $634
CA $6,220 total
CA $6,220 total
includes taxes & fees
Image gallery for Re-listed: Adorable Condo Beverly - Salem - Halloween
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Re-listed: Adorable Condo Beverly - Salem - Halloween
Beverly, MA
5% off
Price is CA $336
CA $336
CA $3,033 total
CA $3,033 total
includes taxes & fees
Image gallery for New 5B3B Single Family with Central AC
9.89.8 out of 10 rating
Exceptional
(28 reviews)
New 5B3B Single Family with Central AC
Arlington, MA
5% off
Price is CA $737
CA $737
CA $6,768 total
CA $6,768 total
includes taxes & fees
Image gallery for Luxury and Modern Apt near Mall/ Hospital
1010 out of 10 rating
Exceptional
(32 reviews)
Luxury and Modern Apt near Mall/ Hospital
Danvers, MA
10% off
Price is CA $333
CA $333
CA $3,055 total
CA $3,055 total
includes taxes & fees
Image gallery for Sunny Dog Friendly Union Sq 1brm
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Sunny Dog Friendly Union Sq 1brm
Somerville, MA
5% off
Price is CA $264
CA $264
CA $2,468 total
CA $2,468 total
includes taxes & fees
Image gallery for Historic Townhouse in the Heart of Boston
9.49.4 out of 10 rating
Exceptional
(35 reviews)
Historic Townhouse in the Heart of Boston
Boston, MA
5% off
Price is CA $784
CA $784
CA $7,260 total
CA $7,260 total
includes taxes & fees
Image gallery for 2BR Downtown Gem| Historic Beverly+Salem |Parking!
1010 out of 10 rating
Exceptional
(27 reviews)
2BR Downtown Gem| Historic Beverly+Salem |Parking!
Beverly, MA
5% off
Price is CA $434
CA $434
CA $3,931 total
CA $3,931 total
includes taxes & fees
Image gallery for Stunning South End/Back Bay Penthouse!
1010 out of 10 rating
Exceptional
(89 reviews)
Stunning South End/Back Bay Penthouse!
Boston, MA
10% off
Price is CA $682
CA $682
CA $6,241 total
CA $6,241 total
includes taxes & fees
Image gallery for Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
Medford, MA
10% off
Price is CA $257
CA $257
CA $2,450 total
CA $2,450 total
includes taxes & fees
Image gallery for 39-SPRING GETAWAY EARLY BIRD 10%! Newly Built & Cozy Townhouse
9.69.6 out of 10 rating
Exceptional
(43 reviews)
39-SPRING GETAWAY EARLY BIRD 10%! Newly Built & Cozy Townhouse
Quincy, MA
19% off
Price is CA $366
CA $366
CA $3,357 total
CA $3,357 total
includes taxes & fees
Image gallery for Historic 1686 Home Near Downtown l 5BR Retreat
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Historic 1686 Home Near Downtown l 5BR Retreat
Beverly, MA
10% off
Price is CA $738
CA $738
CA $6,820 total
CA $6,820 total
includes taxes & fees
Image gallery for 14b-Charming, beautiful 3-bedroom apartment in Boston
9.89.8 out of 10 rating
Exceptional
(8 reviews)
14b-Charming, beautiful 3-bedroom apartment in Boston
Boston, MA
10% off
Price is CA $428
CA $428
CA $4,031 total
CA $4,031 total
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Wine & Cheese Cask
Showing deals for: Nov 2 - Nov 5
Global Luxury Suites Downtown Boston
Sleeps 3 · 1 bedroom
8.08.0 out of 10
Very goodvery good
571 reviews(571 reviews)
The current price is CA $366
CA $366
CA $1,459 total
includes taxes & fees
Temple Place Suites
Sleeps 3 · 1 bedroom
7.07.0 out of 10
Goodgood
256 reviews(256 reviews)
The current price is CA $246
CA $246
CA $1,011 total
includes taxes & fees
Premier Suites - Bay Village
Sleeps 2 · 1 bedroom
6.26.2 out of 10
190 reviews(190 reviews)
The current price is CA $268
CA $268
CA $994 total
includes taxes & fees
Bay Village Suites
Sleeps 1 · 1 bedroom
6.46.4 out of 10
185 reviews(185 reviews)
The current price is CA $182
CA $182
CA $699 total
includes taxes & fees
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Sleeps 2 · 1 bathroom
8.88.8 out of 10
Excellentexcellent
68 reviews(68 reviews)
The current price is CA $636
CA $636
CA $2,252 total
includes taxes & fees
Take An Amazing Vacation! Pet-Friendly Property, Near Liberty Ride Trolley Tour!
Sleeps 4 · 1 bedroom · 1 bathroom
7.67.6 out of 10
Goodgood
12 reviews(12 reviews)
The current price is CA $132
CA $132
CA $493 total
includes taxes & fees
Top rated rentals - Wine & Cheese Cask
Nice trip
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Perfect Stay
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
Amazing host.
1010 out of 10
Exceptionalexceptional
228 reviews(228 reviews)
Beautiful little home in the most perfect town
1010 out of 10
Exceptionalexceptional
133 reviews(133 reviews)
Marblehead trip
1010 out of 10
Exceptionalexceptional
58 reviews(58 reviews)
Wonderful !
1010 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value