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

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746 Best Family Vacation Rentals in Wine & Cheese Cask (Starting from $212)

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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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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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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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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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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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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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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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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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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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
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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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Spacious 3-bedroom 2bath apartment in Somerville
Spacious 3-bedroom 2bath apartment in Somerville
Apartment
Somerville, MA, 02143, United States
1.2k from Wine & Cheese Cask center

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

3 Bedrooms12 Guests
New to Booking
$1232
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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Union Square House
Union Square House
House
Somerville, MA, 02143, United States
1.2k from Wine & Cheese Cask center

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

4 Bedrooms6 Guests
9.6

Exceptional

92 reviews

$366
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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LUX Retreat Home with Yard & Parking
LUX Retreat Home with Yard & Parking
Apartment
Somerville, MA, 02144, United States
1.3k from Wine & Cheese Cask center

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

3 Bedrooms14 Guests
10.0

Exceptional

2 reviews

$1382
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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Serene 4BR 3BA Apt • Harvard/MIT • Sleeps 10+ • Parking Permit Included
Serene 4BR 3BA Apt • Harvard/MIT • Sleeps 10+ • Parking Permit Included
Apartment
Cambridge, MA, 02139, United States
1.3k from Wine & Cheese Cask center

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

4 Bedrooms13 Guests
10.0

Exceptional

1 reviews

$1413
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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Cambridge/Boston 3BR2Bth Parking, W/D, Subway,A/C
Cambridge/Boston 3BR2Bth Parking, W/D, Subway,A/C
Apartment
Somerville, MA, 02143, United States
1.4k from Wine & Cheese Cask center

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

3 Bedrooms8 Guests
9.8

Exceptional

12 reviews

$418
Average price / night
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NEW 9BR6Bth Parking MIT Harvard Boston Walk to T
NEW 9BR6Bth Parking MIT Harvard Boston Walk to T
House
Somerville, MA, USA
1.4k from Wine & Cheese Cask center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

9 Bedrooms23 Guests
New to Booking
$2885
Average price / night
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3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C
3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C
Apartment
Somerville, MA, 02143, United States
1.4k from Wine & Cheese Cask center

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

3 Bedrooms7 Guests
9.4

Superb

13 reviews

$448
Average price / night
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4BR 3BATH Harvard MIT Home
4BR 3BATH Harvard MIT Home
Apartment
Cambridge, MA, USA
1.5k from Wine & Cheese Cask center

Security/Safety, Laundry, Internet, Fireplace/Heating, Parking, Sports/Activities, Air Conditioner

4 Bedrooms14 Guests
New to Booking
$950
Average price / night
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Parking 3BR2Bth, Cambridge/Boston, W/D, Subway,A/C
Parking 3BR2Bth, Cambridge/Boston, W/D, Subway,A/C
Apartment
Somerville, MA, 02143, United States
1.4k from Wine & Cheese Cask center

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

3 Bedrooms8 Guests
9.8

Exceptional

16 reviews

$448
Average price / night
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Cozy 4BR near Boston plus gameroom
Cozy 4BR near Boston plus gameroom
Apartment
Somerville, MA, USA
1.5k from Wine & Cheese Cask center

View, Security/Safety, Internet, Air Conditioner, Parking, Child Friendly

1 Bedroom10 Guests
New to Booking
$750
Average price / night
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Multi-level Townhouse, Harvard, Mit, Red Line
Multi-level Townhouse, Harvard, Mit, Red Line
Apartment
Wine & Cheese Cask, Somerville, Massachusetts, USA
1.5k from Wine & Cheese Cask center

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

2 Bedrooms6 Guests
7.0

Good

3 reviews

$434
Average price / night
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Modern LUX | Deck+ Parking | Near T Harvard/MIT/BU
Modern LUX | Deck+ Parking | Near T Harvard/MIT/BU
Apartment
Cambridge, MA, 02139, United States
1.4k from Wine & Cheese Cask center

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

4 Bedrooms14 Guests
New to Booking
$1651
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 Family Vacation Rentals in Wine & Cheese Cask.

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

Wine & Cheese Cask Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 746 verified family-friendly vacation rentals in Wine & Cheese Cask. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Wine & Cheese Cask vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $212 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Wine & Cheese Cask offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Wine & Cheese Cask are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Wine & Cheese Cask often include amenities such as Child Friendly, Internet, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.