Holliston Vacation Rentals & Ski-in/Ski-out Homes
House
2 Bedrooms
2 Baths
6 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $470/Night
7 Nights - US $3,290
Hotel
- Massachusetts
- ·
- Milford
- 0.89 mi to center
9.3Exceptional
(15 Reviews)
1 Bath
EV Charge Station- Parking
- Air Conditioner
Internet
US $103/Night
7 Nights - US $721
Hotel
9.4Exceptional
(8 Reviews)
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $157/Night
7 Nights - US $1,096
Cottage
1 Bedroom
1 Bath
2 Guests
900 ft²
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $333/Night
7 Nights - US $2,330
Hotel
- Massachusetts
- ·
- Milford
- 1.79 mi to center
7.9Very Good
(208 Reviews)
1 Bath
744.5 ft²
Private Pool- Parking
Pool- Balcony/Terrace
US $139/Night
7 Nights - US $970
Apartment
1 Bedroom
1 Bath
4 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $276/Night
7 Nights - US $1,932
Apartment
- Massachusetts
- ·
- Hopkinton
- 0.19 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
Child Friendly
US $238/Night
7 Nights - US $1,664
House
- Massachusetts
- ·
- Holliston
- 1.14 mi to center
9.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $193/Night
7 Nights - US $1,350
House
- Massachusetts
- ·
- Ashland
- 1.77 mi to center
2 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Child Friendly
Laundry
Security/Safety
US $385/Night
7 Nights - US $2,698
Luxury Places to Stay in Holliston
Over 57+ Luxury Places to Stay in or Near Holliston
House
5 Bedrooms
4 Baths
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $1,656/Night
7 Nights - US $11,595
House
6 Bedrooms
7 Baths
12 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $1,445/Night
7 Nights - US $10,116
House
- Massachusetts
- ·
- Framingham
- 1.13 mi to center
8.6Fabulous
(4 Reviews)
5 Bedrooms
2 Baths
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $755/Night
7 Nights - US $5,284
House
- Massachusetts
- ·
- Holliston
- 2.15 mi to center
9.6Exceptional
(45 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $693/Night
7 Nights - US $4,850
House
- Massachusetts
- ·
- Franklin
- 3.15 mi to center
10.0Exceptional
(13 Reviews)
3 Bedrooms
2 Baths
6 Guests
1380 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $619/Night
7 Nights - US $4,334
House
- Massachusetts
- ·
- Medway
- 0.69 mi to center
4 Bedrooms
2 Baths
6 Guests
3100 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $391/Night
7 Nights - US $2,737
Hotel
- Massachusetts
- ·
- Milford
- 0.82 mi to center
10.0Exceptional
(1 Review)
2 Baths
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $383/Night
7 Nights - US $2,682
Hotel
- Massachusetts
- ·
- Milford
- 0.82 mi to center
10.0Exceptional
(1 Review)
2 Baths
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $383/Night
7 Nights - US $2,682
House
3 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $337/Night
7 Nights - US $2,358
Top-Rated Vacation Rentals with a Pool in Holliston
Over 24+ Top-Rated Vacation Rentals with a Pool in or Near Holliston
Hotel
- Massachusetts
- ·
- Milford
- 0.82 mi to center
10.0Exceptional
(1 Review)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $128/Night
7 Nights - US $899
Hotel
- Massachusetts
- ·
- Milford
- 0.82 mi to center
9.0Exceptional
(2 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $190/Night
7 Nights - US $1,329
Hotel
- Massachusetts
- ·
- Milford
- 0.97 mi to center
8.6Fabulous
(1007 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Kitchen
US $127/Night
7 Nights - US $891
Hotel
- Massachusetts
- ·
- Milford
- 0.82 mi to center
8.6Fabulous
(4 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $134/Night
7 Nights - US $938
Hotel
- Massachusetts
- ·
- Milford
- 1.77 mi to center
8.4Excellent
(1002 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $170/Night
7 Nights - US $1,190
Hotel
- Massachusetts
- ·
- Milford
- 0.80 mi to center
8.2Excellent
(919 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $132/Night
7 Nights - US $924
Hotel
- Massachusetts
- ·
- Milford
- 0.77 mi to center
7.6Very Good
(1013 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $105/Night
7 Nights - US $735
Hotel
- Massachusetts
- ·
- Milford
- 0.85 mi to center
7.5Very Good
(113 Reviews)
1 Bath
- Private Pool
- Parking
- Pool
- Air Conditioner
US $127/Night
7 Nights - US $887
Hotel
- Massachusetts
- ·
- Milford
- 0.80 mi to center
7.4Very Good
(284 Reviews)
8 Baths
293.32 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $128/Night
7 Nights - US $898
Pet-Friendly Vacation Rentals in Holliston
Over 8+ Pet-Friendly Vacation Rentals in or Near Holliston
House
- Massachusetts
- ·
- Ashland
- 2.04 mi to center
9.4Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Internet
- Pet Friendly
- Child Friendly
- Laundry
US $256/Night
7 Nights - US $1,794
Hotel
- Massachusetts
- ·
- Milford
- 1.87 mi to center
7.6Very Good
(282 Reviews)
1 Bath
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $96/Night
7 Nights - US $673
Hotel
- Massachusetts
- ·
- Milford
- 1.90 mi to center
7.6Very Good
(1004 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $112/Night
7 Nights - US $781
House
- Massachusetts
- ·
- Holliston
- 1.47 mi to center
2 Bedrooms
2 Baths
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $143/Night
7 Nights - US $1,002
Hotel
- Massachusetts
- ·
- Milford
- 0.79 mi to center
6.9Good
(366 Reviews)
1 Bath
248.47 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $80/Night
7 Nights - US $557
House
1 Bedroom
4 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $5,184/Night
7 Nights - US $36,286
House
2.0Average
(1 Review)
7 Bedrooms
6 Baths
15 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,249/Night
7 Nights - US $15,742
House
- Massachusetts
- ·
- Franklin
- 2.73 mi to center
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Air Conditioner
- Internet
- Pet Friendly
US $428/Night
7 Nights - US $2,995
Large Vacation Homes & Villas in Holliston
Over 3+ Large Vacation Homes & Villas in or Near Holliston
House
5 Bedrooms
4 Baths
10 Guests
- Internet
- Child Friendly
- Security/Safety
US $800/Night
7 Nights - US $5,597
House
- Massachusetts
- ·
- Framingham
- 1.12 mi to center
10.0Exceptional
(5 Reviews)
5 Bedrooms
2 Baths
10 Guests
2400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $967/Night
7 Nights - US $6,769
House
3.3Average
(3 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Kitchen
- Air Conditioner
- Laundry
TV
US $299/Night
7 Nights - US $2,093
Wheelchair Accessible Vacation Homes in Holliston
Over 15+ Wheelchair Accessible Vacation Homes in or Near Holliston
Hotel
- Massachusetts
- ·
- Milford
- 0.82 mi to center
6.0Good
(2 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $128/Night
7 Nights - US $899
Hotel
- Massachusetts
- ·
- Ashland
- 1.44 mi to center
9.2Exceptional
(80 Reviews)
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $279/Night
7 Nights - US $1,954
US $192/Night
7 Nights - US $1,345
US $192/Night
7 Nights - US $1,345
US $177/Night
7 Nights - US $1,237
US $177/Night
7 Nights - US $1,237
US $128/Night
7 Nights - US $899
US $128/Night
7 Nights - US $899
US $193/Night
7 Nights - US $1,352
Holliston Resorts and Airbnb Homes Under $200
Over 12+ Holliston Resorts and Airbnb Homes Under $200
House
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,315
Hotel
7.7Very Good
(3 Reviews)
4 Baths
339.06 ft²
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $172/Night
7 Nights - US $1,204
Hotel
- Massachusetts
- ·
- Milford
- 0.87 mi to center
9.0Exceptional
(67 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $118/Night
7 Nights - US $827
Apartment
- Massachusetts
- ·
- Ashland
- 1.42 mi to center
2 Bedrooms
1 Bath
6 Guests
- Kitchen
- Air Conditioner
- Internet
Bedding/Linens
US $176/Night
7 Nights - US $1,233
Apartment
- Massachusetts
- ·
- Ashland
- 1.12 mi to center
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $114/Night
7 Nights - US $799
Apartment
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Bedding/Linens
- Security/Safety
US $196/Night
7 Nights - US $1,375
House
- Massachusetts
- ·
- Milford
- 1.18 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $74/Night
7 Nights - US $515
US $191/Night
7 Nights - US $1,336
US $181/Night
7 Nights - US $1,267
Instantly Bookable Vacation Homes in Holliston
Over 7+ Instantly Bookable Vacation Homes in or Near Holliston
Apartment
9.8Exceptional
(16 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $200/Night
7 Nights - US $1,402
US $132/Night
7 Nights - US $923
US $126/Night
7 Nights - US $884
US $126/Night
7 Nights - US $884
US $630/Night
7 Nights - US $4,410
US $630/Night
7 Nights - US $4,410
Apartment
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $209/Night
7 Nights - US $1,466
Book a Last Minute Place to Stay in Holliston
About Holliston Vacation Rentals
Explore over 66 vacation rentals in Holliston with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Holliston for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Holliston. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Holliston tailored to your preferences. On average, these rentals offer 166.67 ft² of space, and are priced at an average of US $403 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Holliston at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Holliston
| Type | Count |
|---|---|
| Vacation Homes | 20 |
| Holiday Apartments | 10 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Holliston
★ Pro Tip: Discover Your Ideal Vacation Rental in Holliston with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Holliston, MA
View the weather forecast for Holliston before booking your Holliston Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Holliston, MA
Sunski offers a large selection of top attractions around Holliston . Research things to do on your vacation before you visit Holliston.
Other Places to Stay in Holliston, MA
Frequently Asked Questions About Holliston?
What are the top vacation rentals in Holliston?
When organizing your trip to Holliston, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Holliston. Peruse our collection of highly-rated properties and secure your reservation today.
- Water access and fire pit. Relax and enjoy the nature!
- Quiet Studio W/King Bed - Home of Boston Marathon
- Relaxing Stay, Two 1BR Units With Pool, Enjoy Nearby Boston Attractions!
- Convenient Stay, Superb Location! 2 Modern Units in Milford, Near Calzone Park
- Breath of Fresh Air! Pet-Friendly, Close to Louisa Lake and Fairbanks Land
- Spacious 3-bedroom apartment in lovely Millis with AC, WiFi
- Spacious Cozy Cabin Style house.
- The Inn at Fireside Tavern Sherborn
- Charming 3-bedroom house in delightful Ashland for your getaway
- Spark by Hilton Milford Boston
Which vacation homes or resorts in Holliston are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Holliston. Enjoy great views, locations and save money with SunSki Resorts.™
- Orchard Room: The Inn at Fireside Tavern Sherborn
- Pond Room: The Inn at Fireside Tavern Sherborn
- Farm Room: The Inn at Fireside Tavern Sherborn
How many SunSkiResorts vacation rentals or resorts are available in Holliston?
Discover the ideal vacation rental in Holliston with SunSki Resorts™. We provide an extensive selection of over 66 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Holliston.
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