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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Rutland vacation homes

A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

1. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is AED 588
AED 958 total
includes taxes & fees
14 Oct - 15 Oct
Angel Sky Challenge
The Cottage is nestled next to the historic Sagendorph Mansion.

2. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
The price is AED 841
AED 957 total
includes taxes & fees
14 Oct - 15 Oct
Cottage by the Castle – Downtown Spencer
A stone wall, a metal gate, and a building with a blue door and a number '74' sign.

3. A Timeless Retreat at Historic Crompton House

A Timeless Retreat at Historic Crompton House
Elm Park
10.0 out of 10, Exceptional, (1 review)
"This is a beautiful property! Great location and amazing hosts! We had everything we needed and were very comfortable. I highly recommend this place!"
United States
Jessica H.
A Timeless Retreat at Historic Crompton House
A two-story residential building with a front porch, a satellite dish, and a small front yard.

4. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is AED 918
AED 2,056 total
includes taxes & fees
19 Oct - 20 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

5. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (2 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is AED 1,377
AED 2,073 total
includes taxes & fees
1 Nov - 2 Nov
4-bedroom house in nice Holden with WiFi, AC
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

6. Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
The price is AED 808
AED 1,623 total
includes taxes & fees
31 Oct - 1 Nov
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A living room with a sofa, a clock, a floor lamp, and a rug.

7. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (55 reviews)
"Easy in and out. Place was dated but clean. The host was welcoming and easy to work with. Parking is good. A little pricy but safe neighborhood."
United States
Thomas M.
The price is AED 592
AED 1,104 total
includes taxes & fees
14 Oct - 15 Oct
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
A lakeside cabin with a dock, a boat, and a second-story deck.

8. Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Westminster
10.0 out of 10, Exceptional, (42 reviews)
"We had a great stay with our family."
United States
Sherri P.
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

9. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"Very clean and readily met the needs of our family of 7 traveling on vacation from Washington DC to Maine. Would stay again."
United States
Jim O.
The price is AED 1,010
AED 1,888 total
includes taxes & fees
14 Oct - 15 Oct
Spacious 4-bedroom with four and half bathrooms
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

10. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
The price is AED 614
AED 787 total
includes taxes & fees
14 Oct - 15 Oct
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
A staircase with wooden steps and black balusters, a potted plant on a side table, and a framed floral artwork on the wall.

11. Spacious 5-bedroom home with three full bathrooms in charming Worcester location

Spacious 5-bedroom home with three full bathrooms in charming Worcester location
Worcester
The price is AED 1,322
AED 1,820 total
includes taxes & fees
27 Oct - 28 Oct
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A modern kitchen with a marble island, stainless steel appliances, and bar stools.

12. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is AED 1,041
AED 2,587 total
includes taxes & fees
14 Oct - 15 Oct
Entire home in Sterling, Massachusetts, United States
A grassy outdoor area with a hammock, chairs, and a stone wall.

13. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (27 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is AED 680
AED 811 total
includes taxes & fees
3 Nov - 4 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

14. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (39 reviews)
"It was a beautiful property. Well-tended and all the amenities. Loved the view in morning and evening of mountains and sun / moon."
United States
Daniel C.
The price is AED 3,636
AED 6,515 total
includes taxes & fees
18 Oct - 19 Oct
Sleeps 15 • Pool • Retreat
A hotel with a central building, outdoor seating area, and a covered patio.

15. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveler
The price is AED 1,010
AED 1,965 total
includes taxes & fees
2 Nov - 3 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

16. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 reviews)
"Pictures don't do this house justice! Great communication from start to finish, very clean house & property, coolest house we've ever stayed at. Hope to stay again!"
United States
Mike T.
The price is AED 973
AED 2,919 total
includes taxes & fees
14 Oct - 15 Oct
Lake House in Sturbridge w/All the Views!
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

17. Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (10 reviews)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
The price is AED 1,194
AED 1,425 total
includes taxes & fees
14 Oct - 15 Oct
Enjoy your stay in an antique home in an antique toy museum!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Rutland Hotel Reviews

northborough inn

northborough inn

10/10 Excellent
"Great experience"
Mayra 2-night trip
Posted less than an hour ago
northborough inn