Vacation Rentals in Wine & Cheese Cask, MA: Compare 10+ Sites & Save

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2312 Best Vacation Rentals in Wine & Cheese Cask (Starting from $167)

A Friendly Inn at Harvard
A Friendly Inn at Harvard
House
Wine & Cheese Cask, Somerville, Massachusetts, USA
0.5k from Wine & Cheese Cask center

B&bs, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

13 Bedrooms2 Guests
8.0

Good

857 reviews

$167
Average price / night
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Lovely 2-bedroom apartment in Cambridge near Harvard and MIT
Lovely 2-bedroom apartment in Cambridge near Harvard and MIT
Apartment
Cambridge, MA, 02138, United States
0.3k from Wine & Cheese Cask center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$619
Average price / night
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Walk to Harvard Square Apartment in Cambridge
Walk to Harvard Square Apartment in Cambridge
Apartment
Cambridge, MA, USA
0.8k from Wine & Cheese Cask center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms5 Guests
9.3

Superb

3 reviews

$681
Average price / night
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Comforts of your home in tranquility by Harvard/MIT
Comforts of your home in tranquility by Harvard/MIT
Apartment
Cambridge, MA, 02138, United States
0.5k from Wine & Cheese Cask center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$1144
Average price / night
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4BR 3Bath Game Room Harvard MIT Apt
4BR 3Bath Game Room Harvard MIT Apt
Apartment
Cambridge, MA, USA
0.8k from Wine & Cheese Cask center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Family

4 Bedrooms16 Guests
New to Booking
$950
Average price / night
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Harvard/MIT: Most loved by repeat guests & long-term guests!
Harvard/MIT: Most loved by repeat guests & long-term guests!
Apartment
Cambridge, MA, 02138, United States
0.5k from Wine & Cheese Cask center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.4

Superb

3 reviews

$691
Average price / night
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Cozy Cambridge Apt
Cozy Cambridge Apt
Apartment
Cambridge, MA, USA
0.9k from Wine & Cheese Cask center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

2 Bedrooms8 Guests
8.7

Fabulous

41 reviews

$293
Average price / night
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New England Charm Meets Modern Luxury, Harvard SQ
New England Charm Meets Modern Luxury, Harvard SQ
Apartment
Cambridge, MA, 02138, United States
0.5k from Wine & Cheese Cask center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$1087
Average price / night
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Cambridge
Cambridge
Apartment
Wine & Cheese Cask, Somerville, Massachusetts, USA
1.0k from Wine & Cheese Cask center

Parking, Air Conditioner, Internet, Pet Friendly, Laundry, Child Friendly

1 Bedroom3 Guests
8.8

Fabulous

2 reviews

$236
Average price / night
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Lux 4 Bedrooms/2 Bathrooms. Walk to Harvard, T line + Free Parking
Lux 4 Bedrooms/2 Bathrooms. Walk to Harvard, T line + Free Parking
Apartment
Somerville, MA, 02143, United States
0.5k from Wine & Cheese Cask center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1163
Average price / night
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1BR Minutes from Union Sq Porter Sq Davis Sq BOS-338
1BR Minutes from Union Sq Porter Sq Davis Sq BOS-338
Apartment
Somerville, USA
1.1k from Wine & Cheese Cask center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$212
Average price / night
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Harvard Square!
Harvard Square!
Apartment
Cambridge, MA, 02138, United States
0.5k from Wine & Cheese Cask center

AC, Dryer, Elevator, Extra Bed, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$922
Average price / night
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Best Location At Harvard University! 4 Bedroom Apartment! Two Units Available!
Best Location At Harvard University! 4 Bedroom Apartment! Two Units Available!
Apartment
Cambridge, MA, USA
1.2k from Wine & Cheese Cask center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering

16 Bedrooms32 Guests
8.8

Fabulous

64 reviews

$577
Average price / night
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New Harvard MIT Boston Luxe 4Bed/2BA
New Harvard MIT Boston Luxe 4Bed/2BA
Apartment
Somerville, MA, 02143, United States
0.6k from Wine & Cheese Cask center

AC, Heater, Laundry, No Smoking, Washer

4 Bedrooms10 Guests
New to Booking
$1525
Average price / night
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Homestay near Boston Harvard MIT
Homestay near Boston Harvard MIT
Apartment
Somerville, MA, USA
1.3k from Wine & Cheese Cask center

Apartments, Accommodations, Parking, Lodgings, Jacuzzis, Places to stay, Family

24 Bedrooms96 Guests
New to Booking
$812
Average price / night
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Sunny Dog Friendly Union Sq 1brm
Sunny Dog Friendly Union Sq 1brm
Apartment
Somerville, MA, 02143, United States
0.6k from Wine & Cheese Cask center

AC, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.8

Exceptional

22 reviews

$456
Average price / night
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3BR2Bth Parking Cambridge Boston W&D Subway AC
3BR2Bth Parking Cambridge Boston W&D Subway AC
House
Somerville, MA, USA
1.4k from Wine & Cheese Cask center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms7 Guests
9.4

Superb

10 reviews

$463
Average price / night
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Cambridge Boston 3BR2Bth Parking W&D Subway AC
Cambridge Boston 3BR2Bth Parking W&D Subway AC
House
Somerville, MA, USA
1.4k from Wine & Cheese Cask center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$684
Average price / night
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4BR 3BA Designer Gem • Sleeps to 12 • Min to Redline T & Boston • Free Parking
4BR 3BA Designer Gem • Sleeps to 12 • Min to Redline T & Boston • Free Parking
Apartment
Cambridge, MA, 02139, United States
0.9k from Wine & Cheese Cask center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$3052
Average price / night
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Parking 3BR2Bth Cambridge Boston W&D Subway AC
Parking 3BR2Bth Cambridge Boston W&D Subway AC
Apartment
Somerville, MA, USA
1.4k from Wine & Cheese Cask center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering

3 Bedrooms8 Guests
9.5

Superb

16 reviews

$450
Average price / night
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Harvard Sq 4BR Loft with 2 Free Parking & Charm
Harvard Sq 4BR Loft with 2 Free Parking & Charm
House
Cambridge, MA, 02138, United States
0.9k from Wine & Cheese Cask center

AC, Arcade, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms12 Guests
New to Booking
$1289
Average price / night
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Union Square Beauty 2 bed/2 bath w/ Private Patio
Union Square Beauty 2 bed/2 bath w/ Private Patio
Apartment
Somerville, MA, 02143, United States
0.9k from Wine & Cheese Cask center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms5 Guests
9.4

Superb

12 reviews

$584
Average price / night
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Spacious Studio near MIT and Harvard
Spacious Studio near MIT and Harvard
Apartment
Cambridge, MA, 02139, United States
1.0k from Wine & Cheese Cask center

AC, Heater, Internet, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

4 reviews

$219
Average price / night
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Harvard MIT Lux | Game Room + Parking + Subway
Harvard MIT Lux | Game Room + Parking + Subway
Apartment
Cambridge, MA, 02139, United States
1.0k from Wine & Cheese Cask center

AC, Arcade, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms16 Guests
New to Booking
$1933
Average price / night
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Modern 3BR House with 2 Parking Spots near Cambridge Boston Harvard MIT
Modern 3BR House with 2 Parking Spots near Cambridge Boston Harvard MIT
House
Cambridge, MA, 02139, United States
1.0k from Wine & Cheese Cask center

AC, Dryer, Heater, Internet, Laundry, Living Area, No Smoking, Washer

3 Bedrooms9 Guests
New to Booking
$1161
Average price / night
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Spacious 2BR 2BA Condo & 2x Parking, Minutes from Central Sq, MIT, Harvard.
Spacious 2BR 2BA Condo & 2x Parking, Minutes from Central Sq, MIT, Harvard.
House
Cambridge, MA, 02139, United States
1.0k from Wine & Cheese Cask center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms5 Guests
9.4

Superb

27 reviews

$693
Average price / night
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Gorgeous 4+ br 3.5 ba Harvard mansion: Cambridge Cosmopolitan
Gorgeous 4+ br 3.5 ba Harvard mansion: Cambridge Cosmopolitan
House
Cambridge, MA, 02140, United States
1.0k from Wine & Cheese Cask center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
10.0

Exceptional

8 reviews

$2303
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Wine & Cheese Cask.

Where to stay in Wine & Cheese Cask? Best neighborhoods & areas

Wine & Cheese Cask Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2312 verified vacation rentals in Wine & Cheese Cask. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Wine & Cheese Cask vary depending on the season, property size, and location. Rates typically start from around $167 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Wine & Cheese Cask include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Wine & Cheese Cask welcome pets. Currently, 44 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Wine & Cheese Cask often include amenities such as Fireplace/Heating, Internet, and Guest Services. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.