Webster Square Vacation Rentals & Ski-in/Ski-out Homes
Condo
- Massachusetts
- ·
- Worcester
- 1.35 mi to center
10.0Exceptional
(34 Reviews)
2 Bedrooms
2 Baths
6 Guests
1950 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $333/Night
7 Nights - US $2,330
Apartment
- Massachusetts
- ·
- Worcester
- 0.24 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
43.06 ft²
- Air Conditioner
Internet
Wheelchair Accessible
US $252/Night
7 Nights - US $1,764
Hotel
- Worcester
- ·
- Central Business District
- 0.18 mi to center
9.4Exceptional
(1004 Reviews)
1 Bath
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $216/Night
7 Nights - US $1,514
Cottage
- Massachusetts
- ·
- Worcester
- 0.95 mi to center
10.0Exceptional
(24 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Hot Tub- Parking
Pool- Balcony/Terrace
US $325/Night
7 Nights - US $2,277
House
- Worcester
- ·
- Forest Grove
- 1.52 mi to center
9.8Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
8 Guests
129.17 ft²
- Parking
View- Air Conditioner
- Internet
US $158/Night
7 Nights - US $1,103
Apartment
- Massachusetts
- ·
- Worcester
- 1.68 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
1111 ft²
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $243/Night
7 Nights - US $1,702
Apartment
- Worcester
- ·
- Forest Grove
- 0.87 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $285/Night
7 Nights - US $1,995
House
- Massachusetts
- ·
- Worcester
- 0.82 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $388/Night
7 Nights - US $2,716
Apartment
- Massachusetts
- ·
- Worcester
- 0.75 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $311/Night
7 Nights - US $2,179
Luxury Places to Stay in Webster Square
Over 102+ Luxury Places to Stay in or Near Webster Square
House
- Worcester
- ·
- Central Business District
- 0.38 mi to center
1 Bedroom
1 Bath
6 Guests
652 ft²
- Air Conditioner
- Internet
- Pet Friendly
Child Friendly
US $826/Night
7 Nights - US $5,781
Apartment
- Massachusetts
- ·
- Worcester
- 1.21 mi to center
9.3Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
14 Guests
1001.04 ft²
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $787/Night
7 Nights - US $5,512
Apartment
- Massachusetts
- ·
- Worcester
- 0.98 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $706/Night
7 Nights - US $4,943
House
- Massachusetts
- ·
- Worcester
- 0.95 mi to center
4 Bedrooms
4 Baths
8 Guests
2895.49 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $696/Night
7 Nights - US $4,869
Apartment
- Massachusetts
- ·
- Worcester
- 1.21 mi to center
4 Bedrooms
2 Baths
14 Guests
10763.91 ft²
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $652/Night
7 Nights - US $4,562
Apartment
- Massachusetts
- ·
- Worcester
- 1.09 mi to center
9.6Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $510/Night
7 Nights - US $3,572
New
Apartment
- Massachusetts
- ·
- Worcester
- 0.62 mi to center
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $509/Night
7 Nights - US $3,565
House
- Worcester
- ·
- Webster Square
- 0.28 mi to center
8.0Excellent
(4 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $507/Night
7 Nights - US $3,552
Apartment
- Massachusetts
- ·
- Worcester
- 1.21 mi to center
9.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
14 Guests
1001.04 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $476/Night
7 Nights - US $3,335
Top-Rated Vacation Rentals with a Pool in Webster Square
Over 10+ Top-Rated Vacation Rentals with a Pool in or Near Webster Square
Hotel
- Worcester
- ·
- Central Business District
- 0.23 mi to center
9.2Exceptional
(1004 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $206/Night
7 Nights - US $1,439
House
- Massachusetts
- ·
- Worcester
- 0.95 mi to center
9.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1205.56 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $289/Night
7 Nights - US $2,023
Hotel
- Worcester
- ·
- Central Business District
- 0.26 mi to center
8.5Fabulous
(250 Reviews)
2 Baths
577.22 ft²
Private Pool
Oceanfront- Breakfast
- Parking
US $232/Night
7 Nights - US $1,623
Hotel
- Worcester
- ·
- Central Business District
- 0.18 mi to center
8.0Excellent
(1003 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $155/Night
7 Nights - US $1,084
Hotel
- Worcester
- ·
- Central Business District
- 0.18 mi to center
7.9Very Good
(478 Reviews)
1 Bath
218.35 ft²
- Private Pool
- Hot Tub
EV Charge Station- Parking
US $243/Night
7 Nights - US $1,700
New
House
- Massachusetts
- ·
- Worcester
- 0.95 mi to center
2 Bedrooms
2 Baths
4 Guests
1700 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $413/Night
7 Nights - US $2,894
New
House
- Massachusetts
- ·
- Worcester
- 0.95 mi to center
2 Bedrooms
2 Baths
4 Guests
1700.7 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
US $403/Night
7 Nights - US $2,822
Apartment
- Massachusetts
- ·
- Cherry Valley
- 3.56 mi to center
8.0Excellent
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Parking
- Pool
Spa
US $199/Night
7 Nights - US $1,393
House
- Massachusetts
- ·
- Cherry Valley
- 2.69 mi to center
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $928/Night
7 Nights - US $6,497
Pet-Friendly Vacation Rentals in Webster Square
Over 19+ Pet-Friendly Vacation Rentals in or Near Webster Square
House
- Massachusetts
- ·
- Cherry Valley
- 1.99 mi to center
10.0Exceptional
(12 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $383/Night
7 Nights - US $2,684
Apartment
- Massachusetts
- ·
- Worcester
- 1.80 mi to center
3 Bedrooms
1 Bath
13 Guests
1097.92 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $336/Night
7 Nights - US $2,354
Apartment
- Massachusetts
- ·
- Worcester
- 2.10 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $449/Night
7 Nights - US $3,145
House
3 Bedrooms
2 Baths
5 Guests
1797.57 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $159/Night
7 Nights - US $1,113
Apartment
- Massachusetts
- ·
- Worcester
- 1.88 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $370/Night
7 Nights - US $2,590
Apartment
- Massachusetts
- ·
- Leicester
- 0.15 mi to center
9.4Exceptional
(11 Reviews)
3 Bedrooms
1 Bath
5 Guests
1100 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $333/Night
7 Nights - US $2,334
Apartment
- Massachusetts
- ·
- Cherry Valley
- 2.09 mi to center
1 Bedroom
2 Baths
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $94/Night
7 Nights - US $657
Apartment
- Massachusetts
- ·
- Worcester
- 1.30 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $544/Night
7 Nights - US $3,811
Apartment
- Massachusetts
- ·
- Worcester
- 1.66 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
13 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $420/Night
7 Nights - US $2,942
Large Vacation Homes & Villas in Webster Square
Over 6+ Large Vacation Homes & Villas in or Near Webster Square
House
- Massachusetts
- ·
- Leicester
- 0.96 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
14 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $402/Night
7 Nights - US $2,812
Bed & Breakfast
- Massachusetts
- ·
- Worcester
- 1.03 mi to center
9.1Exceptional
(262 Reviews)
5 Bedrooms
5 Baths
11 Guests
208.82 ft²
- Parking
- View
- Air Conditioner
- Child Friendly
US $233/Night
7 Nights - US $1,634
House
- Massachusetts
- ·
- Leicester
- 2.02 mi to center
9.8Exceptional
(190 Reviews)
5 Bedrooms
3 Baths
10 Guests
2400 ft²
- Kitchen
- Air Conditioner
- Child Friendly
Laundry
US $330/Night
7 Nights - US $2,310
Apartment
- Massachusetts
- ·
- Worcester
- 1.20 mi to center
6.0Good
(51 Reviews)
17 Bedrooms
1 Bath
4 Guests
301.39 ft²
- Parking
- Kitchen
- Internet
- Child Friendly
US $104/Night
7 Nights - US $725
House
- Worcester
- ·
- Forest Grove
- 1.52 mi to center
8.4Excellent
(6 Reviews)
5 Bedrooms
2 Baths
8 Guests
2392 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $373/Night
7 Nights - US $2,612
Apartment
- Worcester
- ·
- Webster Square
- 1.62 mi to center
1 Bedroom
2 Baths
10 Guests
- Kitchen
Bedding/Linens
US $89/Night
7 Nights - US $623
Wheelchair Accessible Vacation Homes in Webster Square
Over 1+ Wheelchair Accessible Vacation Homes in or Near Webster Square
Hotel
- Worcester
- ·
- Central Business District
- 0.19 mi to center
8.8Fabulous
(308 Reviews)
4 Baths
393.37 ft²
- Breakfast
- EV Charge Station
- Parking
- Balcony/Terrace
US $260/Night
7 Nights - US $1,822
Webster Square Resorts and Airbnb Homes Under $200
Over 43+ Webster Square Resorts and Airbnb Homes Under $200
House
- Massachusetts
- ·
- Worcester
- 1.03 mi to center
9.6Exceptional
(28 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $149/Night
7 Nights - US $1,043
New
Apartment
- Massachusetts
- ·
- Worcester
- 1.60 mi to center
1 Bedroom
1 Bath
2 Guests
204.51 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $138/Night
7 Nights - US $968
Apartment
- Massachusetts
- ·
- Worcester
- 0.76 mi to center
9.4Exceptional
(16 Reviews)
3 Bedrooms
1 Bath
5 Guests
950 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $177/Night
7 Nights - US $1,240
New
Apartment
- Massachusetts
- ·
- Worcester
- 1.60 mi to center
1 Bedroom
1 Bath
2 Guests
204.51 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $128/Night
7 Nights - US $899
Apartment
- Massachusetts
- ·
- Worcester
- 1.45 mi to center
9.0Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $100/Night
7 Nights - US $703
Apartment
- Massachusetts
- ·
- Worcester
- 0.54 mi to center
8.8Fabulous
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $144/Night
7 Nights - US $1,007
Apartment
- Massachusetts
- ·
- Worcester
- 0.72 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Parking
- Kitchen
- Internet
- Child Friendly
US $156/Night
7 Nights - US $1,095
Apartment
- Massachusetts
- ·
- Worcester
- 0.54 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $156/Night
7 Nights - US $1,091
Apartment
- Massachusetts
- ·
- Worcester
- 1.72 mi to center
1 Bedroom
1 Bath
3 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $194/Night
7 Nights - US $1,361
Instantly Bookable Vacation Homes in Webster Square
Over 25+ Instantly Bookable Vacation Homes in or Near Webster Square
Apartment
- Worcester
- ·
- Forest Grove
- 0.70 mi to center
9.8Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $363/Night
7 Nights - US $2,540
Apartment
- Massachusetts
- ·
- Worcester
- 0.95 mi to center
1 Bedroom
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $162/Night
7 Nights - US $1,132
House
- Massachusetts
- ·
- Worcester
- 1.70 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
1 Bath
6 Guests
2300 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $466/Night
7 Nights - US $3,261
Apartment
- Worcester
- ·
- Union HIll
- 0.26 mi to center
9.6Exceptional
(43 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Parking
Skiing- Balcony/Terrace
- Kitchen
US $266/Night
7 Nights - US $1,863
House
- Worcester
- ·
- Forest Grove
- 1.53 mi to center
9.6Exceptional
(15 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $465/Night
7 Nights - US $3,253
House
- Massachusetts
- ·
- Worcester
- 0.90 mi to center
7.8Very Good
(8 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $377/Night
7 Nights - US $2,640
House
- Massachusetts
- ·
- Worcester
- 2.27 mi to center
3 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $37/Night
7 Nights - US $261
Apartment
- Massachusetts
- ·
- Worcester
- 3.82 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $144/Night
7 Nights - US $1,008
House
- Worcester
- ·
- Webster Square
- 0.35 mi to center
9.6Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
600 ft²
- Oceanfront
- Hot Tub
- Parking
Ocean View
US $169/Night
7 Nights - US $1,183
Book a Last Minute Place to Stay in Webster Square
About Webster Square Vacation Rentals
Explore over 111 vacation rentals in Webster Square 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 Webster Square 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 Webster Square. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Webster Square tailored to your preferences. On average, these rentals offer 572.46 ft² of space, and are priced at an average of US $269 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Webster Square 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 Webster Square
| Type | Count |
|---|---|
| Holiday Apartments | 61 |
| Vacation Homes | 39 |
| B&B | 2 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Webster Square
★ Pro Tip: Discover Your Ideal Vacation Rental in Webster Square 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 Webster Square, MA
View the weather forecast for Webster Square before booking your Webster Square 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
Frequently Asked Questions About Webster Square?
What are the top vacation rentals in Webster Square?
When organizing your trip to Webster Square, 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 Webster Square. Peruse our collection of highly-rated properties and secure your reservation today.
- Upscale 4 Bedroom Condo w King Bed Suite
- Bright and Spacious 2BR/2BATH Condo with Parking- Highly recommended by guests
- Shared Hot Tub: Historic Cottage, Walk to Elm Park
- Spacious 4-bedroom with four and half bathrooms
- Brand-new & modern 2 bedrooms and 1.5 baths apt.
- SalsVista 2nd Floor Corner Apt
- Breezy 4BR Worcester Home Pet-Friendly Summer Fun near I-290 & Parks 16-3
- Modern & Spacious 4 Bedroom Single Family Home
- Charming 3-bedroom, 1.5 bath house in Worcester
- The Grand Beam Residence Luxury 3BR + King Suite
Which vacation homes or resorts in Webster Square are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Webster Square. Enjoy great views, locations and save money with SunSki Resorts.™
- Wonderful Worcester House!
- Newly Furnished 4Bedroom Home Near Worcester Airport
- 1 BR Apt walk to MCPHS, WPI, St Vincent Hospital
How many SunSkiResorts vacation rentals or resorts are available in Webster Square?
Discover the ideal vacation rental in Webster Square with SunSki Resorts™. We provide an extensive selection of over 111 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Webster Square.
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