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Compare 15 Cottages in Oakham with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (20)
"This was a very clean property. "
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Trainmaster's Inn - Caboose

9.2 out of 10, Wonderful, (5)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
The price is SAR 563
SAR 1,218 total
includes taxes & fees
27 Apr - 28 Apr
Trainmaster's Inn - Caboose

Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks

10.0 out of 10, Exceptional, (13)
"If you want to relax in a serene lake setting with a spectacular outdoor patio - this is the place to be! Enjoy the lake and get out on the water with kayaks and don’t miss a pontoon boat ride."
Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (2)
"Property is in excellent condition, just the right amount of space for us. "
Brimfield Waterfront cottage

Beautiful & Historic Cottage, Steps to Elm Park

2.5 star property
9.6 out of 10, Exceptional, (5)
"place was very nice and owners where very responsive, and you can't beat the location. great restaurants a few blocks away.I been looking for a place to stay when I come visit my sister and this might be it."
Beautiful & Historic Cottage, Steps to Elm Park

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (18)
"This cute cottage served our family of 5 adults. It was clean and well decorated. Would definitely recommend. "
Cottage on Partridge Pond

Sun-dappled Retreat - Walk to Wickaboag Lake!

3.0 star property
Sun-dappled Retreat - Walk to Wickaboag Lake!

Worcester Home on Indian Lake w/ Shared Boat Dock!

3.0 star property
Worcester Home on Indian Lake w/ Shared Boat Dock!

Stunning Sterling Sanctuary: Unwind on the Water!

3.0 star property
Stunning Sterling Sanctuary: Unwind on the Water!

Grand Worcester Getaway w/ Large Private Yard!

3.0 star property
Grand Worcester Getaway w/ Large Private Yard!

Waterfront New England House on Wickaboag Lake!

3.0 star property
Waterfront New England House on Wickaboag Lake!

Beach Front Stay on Fully Recreational Lake at the base of Wachusett Mountain

Beach Front Stay on Fully Recreational Lake at the base of Wachusett Mountain

Vibrant Sterling Lakefront Lodge w/ Kayaks

3.0 star property
Vibrant Sterling Lakefront Lodge w/ Kayaks

Dog-friendly Fitchburg Vacation Rental, Hike & Ski

3.0 star property
Dog-friendly Fitchburg Vacation Rental, Hike & Ski

Charming Worcester Retreat w/ Private Pool!

3.0 star property
Charming Worcester Retreat w/ Private Pool!
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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Other property types in Oakham

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

9.8 out of 10, Exceptional, (21)
"Love this place. Quiet and has everything you need to feel welcome. Thank you to Eben the host as he is always on top of things"
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (182)
"The house is so clean has everything we need to host Christmas, beautiful lake view close to everything and owner is on site if you need anything "
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Home Away from Home!

10.0 out of 10, Exceptional, (2)
"Thank you for our little stay-cation! The property was beautiful and was exactly as expected. Plenty of rooms and bathrooms. My only wish was for more mirrors for us all to do our make up. But we made it work. "
The price is SAR 698
SAR 1,498 total
includes taxes & fees
28 Apr - 29 Apr
Home Away from Home!
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.