Rutland Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Rutland

Residences at Solomon Pond

3.5 star property
8.0 out of 10, Very good, (134)
"Love it"
The price is AU$199
includes taxes & fees
26 Nov - 27 Nov
Residences at Solomon Pond

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

One Bedroom Queen Suite with sofa bed and fully equipped kitchen

6.0 out of 10, (1)
"Put my and my family of 5 in the wrong room, which they easily changed to a 2x2 as i had rented. Sunday afternoon the "maintence" man let himself in as we are in the room letting our dog outside. He didnt speak much english. Not sure what he was doing but he looked in our electric oven and than left. We didnt feel real safe so when we left we made sure to tske any valubles out and rigged the room to see of people had come in again. "
The price is AU$248
includes taxes & fees
6 Dec - 7 Dec
One Bedroom Queen Suite with sofa bed and fully equipped kitchen

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (29)
"This was an amazing property! My mother stayed there and said it was cozy and she felt at home. The place was clean, cozy, and quaint! Would definitely stay there again!"
The price is AU$375
includes taxes & fees
27 Nov - 28 Nov
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful Renovated CASTLE 5Bedrooms 2bath near BOSTON

8.0 out of 10, Very good, (2)
"House was comfortable and cozy. Recommend this place for anyone looking to stay in the Marlborough area. "
Beautiful Renovated CASTLE 5Bedrooms 2bath near BOSTON

Leicester Lake Front Home, Come Relax!

10.0 out of 10, Exceptional, (23)
"Perfect for a family getaway. Rooms upstairs so meeting in kitchen and living rooms to get together works. View of the sunset lovely and set up for evening snores and relaxing very nice. "
Leicester Lake Front Home, Come Relax!

BRAND NEW Designer 2br*SMART TVs*WD*Free Parking*Free Fios Wifi* Close to BOSTON

8.0 out of 10, Very good, (1)
"Did what we needed it to do, was very clean and peaceful. Response time could’ve been better on communication. But overall was a great stay and would definitely stay again."
The price is AU$1,060
includes taxes & fees
26 Nov - 27 Nov
BRAND NEW Designer 2br*SMART TVs*WD*Free Parking*Free Fios Wifi* Close to BOSTON

Fall Villa near Treehouse Brewery & Amazon Warehouse with King Beds

8.4 out of 10, Very good, (21)
"It was nice. Not really waterfront. Pool was nice on a hot day. FYI- Google maps took us to the wrong house. Glad the neighbor didn't mind us at the door at 10 p.m. Plenty of room for family gathering."
The price is AU$1,303
includes taxes & fees
9 Dec - 10 Dec
Fall Villa near Treehouse Brewery & Amazon Warehouse with King Beds

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (23)
"The property allowed for my extended family to gather under one roof and spend quality time together in a beautiful and quaint setting. "
Luxury Home, Pool, fireplace

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

9.4 out of 10, Exceptional, (16)
"Place was pristine, great location on the lake. Beautiful scenery with the mountains, used the kayaks to get around the lake and catch some fish! My son and i caught pickerel, perch, bass, crappies, and pumkinseeds. Quick drive from Boston @ a little over a hour."
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Near BOSTON - Cozy and Renovated 4 Beds 2 bath Home w/ Backyard FREE WIFI 6.

9.4 out of 10, Exceptional, (3)
"The townhouse was beautiful and quiet; a great neighborhood. I especially liked the privacy and the set up to get in and unlock the doors. Would definitely recommend. "
The price is AU$1,478
includes taxes & fees
26 Nov - 27 Nov
Near BOSTON - Cozy and Renovated 4 Beds 2 bath Home w/ Backyard FREE WIFI 6.

Lake Adjacent 3-Bedroom Family Home Close to Wachusett Mountain!

9.8 out of 10, Exceptional, (85)
"Home was clean and comfortable. My extended family and I stayed two nights for a wedding in the area and a good time was had by all. No complaints with the accommodations and the hosts communicated well."
Lake Adjacent 3-Bedroom Family Home Close to Wachusett Mountain!

Spacious Massachusetts Apartment #2

9.4 out of 10, Exceptional, (15)
"The apartment was clean, stocked with all you need and the location was just off the Main Street so stores and restaurants were walkable. Ample parking behind the unit. Comfortable bedrooms and furniture. "
Spacious Massachusetts Apartment #2

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

10.0 out of 10, Exceptional, (12)
"We had a great time. The house was very nice and clean. The lake was really lovely for boating and swimming."
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (180)
"Overall a wonderful stay. This is a duplex and the owner lives next door. Nice neighborhood and beautiful view"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Relaxing Retreat

9.8 out of 10, Exceptional, (24)
"The property was very good. A washer and dryer would have been handy."
Relaxing Retreat

Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!

10.0 out of 10, Exceptional, (72)
"We had a lovely stay at this beautiful lakeside retreat. The view was incredible, the home was tastefully decorated and extremely clean. You have thought of everything. This is truly a 10 out of 10! Thank you so much for your kindness and wonderful communication. We couldn't have asked for anything better. We had such a wonderful weekend. We are sure that everyone staying in this home will have a wonderful time."
Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!

Quiet and Cozy Campground Cabin 2 near the lake

9.0 out of 10, Wonderful, (2)
"The check in and out times were very strange. Also I’d suggest bringing your own wood you can buy theirs but they don’t dry it out and it doesn’t burn completely or correctly so the campfire was very very very small and mostly smoke. It is cute and the cabin was a lot smaller then expected but still had a good time didn’t get to enjoy it all because again it’s like there wasn’t enough time. "
Quiet and Cozy Campground Cabin 2 near the lake

Large relaxing house in 25 acres of private woods with lake access.

10.0 out of 10, Exceptional, (16)
"Excellent home in the woods. All as advertised, my family and I thoroughly enjoyed it. Communication with the owner was excellent. 10/10, we’ll be back next time we’re in the area"
Large relaxing house in 25 acres of private woods with lake access.

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (8)
"It's not luxury, but it's 8,437 times better than a hotel. Hung out by the fire pit after work. Nice neighborhood."
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
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.
Don't see what you're looking for?
See all available properties in Rutland
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Rutland you may be interested in

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
8.6 out of 10, Excellent, (811)
"Amazing "
The price is AU$274
includes taxes & fees
2 Dec - 3 Dec
Great Wolf Lodge Boston / Fitchburg, MA

Wellsworth Hotel

3.0 star property
9.2 out of 10, Wonderful, (1021)
"Has a nice pool area and games for kids in restaurant"
The price is AU$178
includes taxes & fees
3 Dec - 4 Dec
Wellsworth Hotel

Courtyard by Marriott Boston Marlborough

3.0 star property
8.6 out of 10, Excellent, (1007)
"Excellent in every aspect "
The price is AU$230
includes taxes & fees
21 Dec - 22 Dec
Courtyard by Marriott Boston Marlborough
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury : This holiday home rental outside of Rutland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Rutland State Park. Wachusett Mountain State Reservation and Wachusett Mountain Ski Area 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.