Rutland Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Rutland

Residences at Solomon Pond

3.5 star property
Marlborough
8.2 out of 10, Very good, (220)
"The room are ideal and comfortable, there was no smoke smell. It was a cozy stay. The price was affordable too. "
United States
Jeff
Residences at Solomon Pond

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Spencer
10.0 out of 10, Exceptional, (199)
"Great time spent with family"
Canada
Marianne B.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Relaxing, Holiday Retreat, Pool, fireplace

Brimfield
10.0 out of 10, Exceptional, (32)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
United States
Danneel A.
Relaxing, Holiday Retreat, Pool, fireplace

Beautiful Lakefront Home with Private Beach

Shrewsbury
9.4 out of 10, Exceptional, (181)
"Great location for the family. Grandson enjoyed fishing and family swimming, cookouts and fire pit. "
United States
PeterJanet S.
Beautiful Lakefront Home with Private Beach

Spacious 4-bedroom with four and half bathrooms

Worcester
10.0 out of 10, Exceptional, (5)
"We had room for each of the adults, which included adult children. At these ages they no longer want to share a bed or bathroom with anyone. Perfect that we could come together, but have our own separate spaces. Very clean and comfortable with everything you need."
United States
Harmony F.
The price is NZ$922
includes taxes & fees
1 Dec - 2 Dec
Spacious 4-bedroom with four and half bathrooms

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

2.0 star property
Ware
10.0 out of 10, Exceptional, (3)
"We had a great time the place was clean and the owner was nice. I would definitely recommend."
United States
Laura B.
The price is NZ$286
includes taxes & fees
25 Nov - 26 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

West Brookfield
10.0 out of 10, Exceptional, (15)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

2.0 star property
Sturbridge
The price is NZ$758
includes taxes & fees
25 Nov - 26 Nov
Cozy Chic Countryside Haven - Sleeps 4 , Firepit

1 Mi to Downtown & Palladium: Worcester Getaway!

3.0 star property
Worcester
10.0 out of 10, Exceptional, (1)
"The place was amazing, just needed a few updates and repairs, but nothing that made our stay bad or inconvenient. "
United States
Michelle
1 Mi to Downtown & Palladium: Worcester Getaway!

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

Sturbridge
9.8 out of 10, Exceptional, (88)
"Very Clean, great location"
United States
Anonymous traveller
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Home Near Skiing & Downtown Worcester

3.0 star property
Worcester
Home Near Skiing & Downtown Worcester

Lake House in Sturbridge w/All the Views!

Sturbridge
9.8 out of 10, Exceptional, (19)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
Lake House in Sturbridge w/All the Views!

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

Westminster
10.0 out of 10, Exceptional, (23)
"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "
United States
Michael T.
The price is NZ$921
includes taxes & fees
1 Dec - 2 Dec
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Home Away from Home!

Worcester
9.4 out of 10, Exceptional, (14)
"The property was nice and accommodating for my family! "
United States
Ykeca M.
The price is NZ$710
includes taxes & fees
25 Nov - 26 Nov
Home Away from Home!

Explore Dtwn, Parks & Colleges: Cozy Worcester Apt

3.0 star property
Worcester
Explore Dtwn, Parks & Colleges: Cozy Worcester Apt

Spacious Massachusetts Apartment #2

West Brookfield
9.0 out of 10, Wonderful, (28)
"We used both apartments for time with extended family. Nice to be in the same building."
United States
Tyler K.
The price is NZ$539
includes taxes & fees
30 Nov - 1 Dec
Spacious Massachusetts Apartment #2

Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

Douglas
10.0 out of 10, Exceptional, (135)
"We had an amazing stay.Very peaceful. It was so nice to be able to have our dog with us. Very enjoyable vacation. "
United States
Ann Marie B.
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

Indian Lake House

Worcester
7.2 out of 10, Good, (5)
"My stay was cozy! Loved the character."
United States
Elizabeth
Indian Lake House

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Shrewsbury
9.8 out of 10, Exceptional, (39)
"Our stay was wonderful. The house was adorable and had everything we needed. The host was always on top of messaging back if we had a question and was very polite. "
United States
Traci M.
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Westminster
9.6 out of 10, Exceptional, (28)
"Nice location and a very cool place to stay "
United States
Samson M.
The price is NZ$667
includes taxes & fees
9 Dec - 10 Dec
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
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.

Black Friday Sale

Save up to 40% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Rutland Hotel Reviews

Find out more about Rutland

Everything you need to know about Rutland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rutland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rutland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Rutland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rutland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rutland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rutland holiday rentals we have selected for you start as low as NZ$286 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Rutland rentals

At Expedia, we put the best Rutland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rutland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rutland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rutland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Spacious 4-bedroom with four and half bathrooms: This holiday home rental outside of Rutland is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Rutland?

While exploring the area, visit family-friendly sights like Davis' Farmland & Mega Maze, 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.