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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, (19)
"for skiing wachusetts five minutes to mt..nice views from cottage on the shore -wyman pond"
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Trainmaster's Inn - Caboose

9.6 out of 10, Exceptional, (4)
"We felt right at home the minute we walked thru the door! Its the most unique place we have ever stayed. The caboose had so many of the original feature. The Innkeepers are readily available and very kind.The outside fire pit area was enjoyed nightly. "
The price is AED 551
AED 1,189 total
includes taxes & fees
8 Apr - 9 Apr
Trainmaster's Inn - Caboose

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

10.0 out of 10, Exceptional, (13)
"Property better than expected! The host, Joe and his wife could not be any more accommodating. So Pleasant. House clean, plenty of room, amazing views of the lake and the mountains. Outdoor space was spectacular and we loved the outdoor kitchen space. Lake tour on their boat was so much fun. We all relaxed, kayaked and enjoyed our time so much! This is a must if looking for a nice house on a lake for your next getaway."
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)
"We were visiting Worcester for Holy Cross Family Weekend. Looking for an alternative to booking 2 overpriced hotel rooms, I found this adorable "
Beautiful & Historic Cottage, Steps to Elm Park

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (18)
"This is the second time we have rented the cottage. It is such a delightful place to stay and the hosts provide such lovely amenities, that I would say it's one of the best rental experiences we've encountered. "
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

Charming Worcester Retreat w/ Private Pool!

3.0 star property
Charming Worcester Retreat w/ Private Pool!

Dog-friendly Fitchburg Vacation Rental, Hike & Ski

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

Vibrant Sterling Lakefront Lodge w/ Kayaks

3.0 star property
Vibrant Sterling Lakefront Lodge w/ Kayaks
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)
"The apartment was very clean and cozy but if you are tall watch out for the low ceilings. Being in an old home it has some wonderful character! The bed was very comfortable as well and has a nice living room with TV. I would highly recommend this place to stay. The host is also very receptive and on top of everything, thank you Ebenezer."
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (13)
"This was our second time and definitely not the last. Great location for the ski week. Has everything you need. Pet friendly which is a big plus for us. Welcoming basket very much appreciated. "
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (183)
"We have used this property for over 4 years now. Just love it and the o"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
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.