Rutland Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Rutland holiday rentals

A wooden cabin bedroom with a bed, a nightstand, a lamp, and a bunk bed.

1. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is HK$2,746
HK$5,854 total
includes taxes & fees
8 Nov - 9 Nov
The Christmas Cottage, 4BR New England Escape
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

2. 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, (3 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 HK$2,942
HK$4,196 total
includes taxes & fees
6 Nov - 7 Nov
4-bedroom house in nice Holden with WiFi, AC
A modern hotel lobby with a seating area, a bar, and a kitchen.

3. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (268 reviews)
"Friendly front desk. Clean and pleasant room. Would stay again."
United States
Tae
The price is HK$911
HK$1,017 total
includes taxes & fees
17 Nov - 18 Nov
Residences at Solomon Pond
The Cottage is nestled next to the historic Sagendorph Mansion.

4. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is HK$1,616
HK$1,748 total
includes taxes & fees
8 Nov - 9 Nov
Cottage by the Castle – Downtown Spencer
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

5. Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Westminster
10.0 out of 10, Exceptional, (40 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is HK$1,765
HK$3,847 total
includes taxes & fees
11 Nov - 12 Nov
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

6. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
9.0 out of 10, Wonderful, (2 reviews)
"Nice and very clean. Host communicated fast and helpful."
United States
Ekaterina
The price is HK$628
HK$827 total
includes taxes & fees
6 Nov - 7 Nov
Clean & Cozy Private-3 floor_R 2
Living area

7. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is HK$1,167
HK$2,782 total
includes taxes & fees
9 Nov - 10 Nov
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Two Adirondack chairs on a wooden deck with a view of a lake and trees.

8. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
3.0 star property
Worcester
The price is HK$1,758
HK$3,550 total
includes taxes & fees
22 Nov - 23 Nov
Worcester Lakefront Cottage Apt w/ Shared Dock!
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

9. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
8.8 out of 10, Excellent, (3 reviews)
"Rented the property to attend a series of events at Clark University. Literally walking distance to the school so it was quite convenient. Apartment was clean, beds were comfortable. Being able to park three cars in the driveway was a huge plus as street parking near the apartment was extremely challenging. Being a Clark alum, was quite familiar with the neighborhood so I knew what to expect. Felt completely safe in the apartment as every door to the hallways had sufficient locks. We did blow a...
United States
Elyse D.
The price is HK$912
HK$2,381 total
includes taxes & fees
8 Nov - 9 Nov
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A two-story house with a central entrance, a brick foundation, and a large front yard.

10. 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 HK$1,255
HK$1,939 total
includes taxes & fees
6 Nov - 7 Nov
Angel Sky Challenge
A living room with two sofas, a coffee table, and a bookshelf.

11. Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
8.0 out of 10, Very good, (1 review)
"We did not receive information on how to enter the property until we arrived and called the owner. There was a lot of poison ivy growing in our parking area."
United States
Sharon
The price is HK$1,462
HK$1,736 total
includes taxes & fees
17 Nov - 18 Nov
Heart of Shrewsbury St – 2BR Stay
A neatly made bed with rolled towels, a bedside table with a lamp, and a large mirror on the wall.

12. Newly Refreshed 3bd Spacious Unit Minutes from 290

Newly Refreshed 3bd Spacious Unit Minutes from 290
Franklin Plantation
9.4 out of 10, Exceptional, (3 reviews)
"The communication was wonderful. There were some things that needed to be addressed and they were.We would definitely rent again! The space is very spacious and clean"
United States
Anonymous traveller
The price is HK$1,349
HK$2,586 total
includes taxes & fees
12 Nov - 13 Nov
Newly Refreshed 3bd Spacious Unit Minutes from 290
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

13. 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)
"Great, clean location to stay."
United States
Mike O.
The price is HK$2,157
HK$3,672 total
includes taxes & fees
9 Nov - 10 Nov
Spacious 4-bedroom with four and half bathrooms
A modern kitchen with a marble island, white cabinetry, and pendant lighting.

14. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is HK$2,471
HK$5,582 total
includes taxes & fees
9 Nov - 10 Nov
Entire home in Sterling, Massachusetts, United States
A modern living room with a flat-screen TV, a sofa, and two armchairs. There is a dining area with a kitchen in the background.

15. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
9.8 out of 10, Exceptional, (7 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
The price is HK$1,506
HK$3,060 total
includes taxes & fees
8 Nov - 9 Nov
12B-Cozy 3BR Apartment with Koi Pond in Worcester
A grassy outdoor area with a hammock, chairs, and a stone wall.

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

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.6 out of 10, Exceptional, (28 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
The price is HK$1,271
HK$1,451 total
includes taxes & fees
9 Nov - 10 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

17. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (4 reviews)
"Gorgeously decorated and ultra-clean. Was the perfect rental for my sisters wedding at Salem Cross Inn"
United States
Trish N.
The price is HK$1,593
HK$2,865 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A residential building with a wooden balcony and a window.

18. Two Bedroom Guesthouse near many attractions pet friendly with private deck

Two Bedroom Guesthouse near many attractions pet friendly with private deck
Gardner
10.0 out of 10, Exceptional, (3 reviews)
"Cute little guesthouse. Super clean and lovely decorated."
United States
Kristin R.
The price is HK$1,165
HK$2,440 total
includes taxes & fees
1 Dec - 2 Dec
Two Bedroom Guesthouse near many attractions pet friendly with private deck
A living room with a TV, a sofa, a chair, a lamp, and a window with sheer curtains.

19. Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
4.0 out of 10, (3 reviews)
The price is HK$698
HK$907 total
includes taxes & fees
26 Nov - 27 Nov
Clean & Cozy Private room - 3 floor_R 1
A spacious living room with a high ceiling, a wooden floor, a black sofa, a white armchair, a small round table, and a window with curtains.

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

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
United States
Laura P.
The price is HK$2,005
HK$2,474 total
includes taxes & fees
6 Nov - 7 Nov
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
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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Find out more about Rutland

Search for holiday rentals in Rutland on Expedia! You can easily find your home rentals, villas, holiday apartments in Rutland using one of the methods below:

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Frequently Asked Questions

Are there holiday rentals in Rutland?

Yes, there are holiday rentals close to the most popular sights in Rutland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Rutland has to offer?

Home Away from Home!: This holiday home rental outside of Rutland offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

What’s there to see and do in Rutland?

While exploring the area, visit family-friendly sights like Great Wolf Lodge Waterpark, or get outside and enjoy nature at Tower Hill Botanic Garden. Rutland State Park and Wachusett Mountain State Reservation are a couple of places you'll find in the wider area.

What’s a holiday rental in Rutland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rutland. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.