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Massachusetts Villas & Holiday Homes

Escape to Massachusetts' stunning coastline, vibrant cities, and scenic countryside with our curated collection of villas. Find your perfect Cape Cod or Boston getaway today!

Villas in Massachusetts

Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, saunaVilla Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa/pools, and spa
4.6/5
£102  night
4
1
1
Details View Offers
LUXURY BERKSHIRES RETREAT - Family Compound! - 2 separate but attached homes!
5.0/5
£279  night
12
6
5
Details View Offers
Chic Villa Oasis by Mohegan Sun wChic Villa Oasis by Mohegan Sun w/ Pool & Hot Tub/ Pool & Hot Tub
£148  night
3
1
1
Details View Offers
Vermont Vacation Villa—Grapevine Getaway
4.5/5
£430  night
14
7
1
Details View Offers
Best Place in Town
£3483  night
10
5
7
Details View Offers
Spacious 6-bedroom luxury villa on edge of Nantucket Nature reserve; full gym.
£3684  night
14
6
9
Details View Offers
For Business and Pleasure Travelers. Pink room.
£57  night
2
1
2
Details View Offers
Mansion at the Highlands
4.9/5
£774  night
12
7
7
Details View Offers
Secluded 20 acre 10BR ultra contemporary retreat
5.0/5
£1098  night
14
10
3
Details View Offers
Cozy newly renovated condo, in Norwich, CT. 3 mins from Mohegan Sun Casino.
4.3/5
£147  night
6
1
1
Details View Offers
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
4.9/5
£114  night
4
1
1
Details View Offers
Winthrop Estate - 1925 Charm & Modern Luxury
£2522  night
24
12
11
Details View Offers
Unique natural waterfront - unforgettable vacation
5.0/5
£866  night
12
6
3
Details View Offers
BONNET OASIS
5.0/5
£941  night
10
4
2
Details View Offers
Mayflower Beach Villas - Seagull
5.0/5
£440  night
10
3
3
Details View Offers
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
5.0/5
£132  night
4
1
1
Details View Offers
Retreat in Style: Luxury for Family & Friends
5.0/5
£582  night
12
5
5
Details View Offers
Dennis Village Stay America's Scenic Rt 6A Mayflower Beach & Apres Poolside
£166  night
3
1
1
Details View Offers
Vrbo Property
4.9/5
£290  night
7
3
2
Details View Offers
Private Penthouse Paradise
4.0/5
£110  night
5
2
2
Details View Offers

Why a holiday villa in Massachusetts

Massachusetts is a treasure trove of experiences waiting to be discovered from its vibrant cities like Boston and Provincetown to its stunning coastlines and scenic countryside. With a villa holiday in Massachusetts, you can immerse yourself in the state's unique blend of rich history, beautiful landscapes, and warm hospitality.

Whether you're looking for a relaxing beach vacation, an action-packed adventure, or a cultural experience that combines historic charm with modern flair, Massachusetts has something for everyone. From sailing on Martha's Vineyard to exploring the Freedom Trail in Boston, every moment of your villa holiday will be filled with unforgettable memories.

When to rent a villa in Massachusetts

Massachusetts is known for its distinct seasonal changes, each with its own unique charm. If you're looking for warm weather and beach activities, summer (June to August) is the perfect time to visit, with average highs ranging from 75°F to 82°F (24°C to 28°C). The Cape Cod and Islands regions are particularly popular during this time, with lively towns, beautiful beaches, and outdoor events like concerts and fireworks displays. However, if you're looking for a more relaxed atmosphere and lower prices, consider visiting in the spring (April to May) or autumn (September to October), when the weather is mild and pleasant, with average highs ranging from 55°F to 65°F (13°C to 18°C).

If you don't mind cooler temperatures and enjoy winter activities like skiing, snowshoeing, and cozying up by a fireplace, Massachusetts has a lot to offer during the winter months (December to March). Many of the state's ski resorts, such as Jiminy Peak and Wachusett Mountain, offer world-class skiing and snowboarding opportunities. Additionally, many towns and cities host festive events and activities like holiday markets, parades, and ice skating rinks, making it a great time to experience Massachusetts' charm in a more intimate setting. Whatever the season, you're sure to find a wonderful villa holiday experience in Massachusetts!

Where to go in Massachusetts

Massachusetts offers a diverse range of experiences across its various regions, each with its own unique charm. If you're looking for a lively atmosphere, consider staying on Cape Cod or Nantucket Island, where vibrant towns like Provincetown and Falmouth offer a great selection of restaurants, bars, and shops. For a more relaxed pace, head to the South Shore, where picturesque towns like Cohasset and Scituate are perfect for quiet walks and waterfront strolls.

Alternatively, explore the coastal regions of Massachusetts, such as Plymouth or Cape Ann, which boast stunning beaches, scenic hiking trails, and historic sites like the Mayflower Compact. The Berkshires in western Massachusetts offer a more rural experience, with picturesque towns like Lenox and Stockbridge providing easy access to cultural attractions, outdoor activities, and delicious farm-to-table cuisine. Each region has its own distinct character, so you're sure to find the perfect fit for your villa holiday in Massachusetts.

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Family friendly villas
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Villas near golf course
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Private pool villas
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Villas in Massachusetts

Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, saunaVilla Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa/pools, and spa
4.6/5
£102  night
4
1
1
Details View Offers
LUXURY BERKSHIRES RETREAT - Family Compound! - 2 separate but attached homes!
5.0/5
£279  night
12
6
5
Details View Offers
Chic Villa Oasis by Mohegan Sun wChic Villa Oasis by Mohegan Sun w/ Pool & Hot Tub/ Pool & Hot Tub
£148  night
3
1
1
Details View Offers
Vermont Vacation Villa—Grapevine Getaway
4.5/5
£430  night
14
7
1
Details View Offers
Best Place in Town
£3483  night
10
5
7
Details View Offers
Spacious 6-bedroom luxury villa on edge of Nantucket Nature reserve; full gym.
£3684  night
14
6
9
Details View Offers
For Business and Pleasure Travelers. Pink room.
£57  night
2
1
2
Details View Offers
Mansion at the Highlands
4.9/5
£774  night
12
7
7
Details View Offers
Secluded 20 acre 10BR ultra contemporary retreat
5.0/5
£1098  night
14
10
3
Details View Offers
Cozy newly renovated condo, in Norwich, CT. 3 mins from Mohegan Sun Casino.
4.3/5
£147  night
6
1
1
Details View Offers
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
4.9/5
£114  night
4
1
1
Details View Offers
Winthrop Estate - 1925 Charm & Modern Luxury
£2522  night
24
12
11
Details View Offers
Unique natural waterfront - unforgettable vacation
5.0/5
£866  night
12
6
3
Details View Offers
BONNET OASIS
5.0/5
£941  night
10
4
2
Details View Offers
Mayflower Beach Villas - Seagull
5.0/5
£440  night
10
3
3
Details View Offers
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
5.0/5
£132  night
4
1
1
Details View Offers
Retreat in Style: Luxury for Family & Friends
5.0/5
£582  night
12
5
5
Details View Offers
Dennis Village Stay America's Scenic Rt 6A Mayflower Beach & Apres Poolside
£166  night
3
1
1
Details View Offers
Vrbo Property
4.9/5
£290  night
7
3
2
Details View Offers
Private Penthouse Paradise
4.0/5
£110  night
5
2
2
Details View Offers