Search Cottages in Oakham

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

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

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

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

10.0 out of 10, Exceptional, (14)
"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
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Aerial view

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

9.4 out of 10, Exceptional, (23)
"This was a very clean property. "
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Cottage on Partridge Pond
Interior

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (19)
"This cute cottage served our family of 5 adults. It was clean and well decorated. Would definitely recommend. "
Cottage on Partridge Pond
Trainmaster's Inn - Caboose
Private kitchen

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 AED 551
AED 1,193 total
includes taxes & fees
4 Jun - 5 Jun
Trainmaster's Inn - Caboose
Beautiful & Historic Cottage, Steps to Elm Park
Terrace/patio

Beautiful & Historic Cottage, Steps to Elm Park

2.5 star property
9.8 out of 10, Exceptional, (9)
"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
Beautiful & Historic Cottage, Steps to Elm Park
Interior

Beautiful & Historic Cottage, Steps to Elm Park

3.0 star property
Beautiful & Historic Cottage, Steps to Elm Park
Sun-dappled Retreat - Walk to Wickaboag Lake!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Sun-dappled Retreat - Walk to Wickaboag Lake!

3.0 star property
Sun-dappled Retreat - Walk to Wickaboag Lake!
Charming Worcester Retreat w/ Private Pool!
Interior

Charming Worcester Retreat w/ Private Pool!

3.0 star property
Charming Worcester Retreat w/ Private Pool!
Dog-friendly Fitchburg Vacation Rental, Hike & Ski
Interior

Dog-friendly Fitchburg Vacation Rental, Hike & Ski

3.0 star property
Dog-friendly Fitchburg Vacation Rental, Hike & Ski
Home Near Skiing & Downtown Worcester
Interior

Home Near Skiing & Downtown Worcester

3.0 star property
Home Near Skiing & Downtown Worcester
Worcester Home on Indian Lake w/ Shared Boat Dock!
House (3 Bedrooms) | Interior

Worcester Home on Indian Lake w/ Shared Boat Dock!

3.0 star property
Worcester Home on Indian Lake w/ Shared Boat Dock!
Vibrant Sterling Lakefront Lodge w/ Kayaks
Interior

Vibrant Sterling Lakefront Lodge w/ Kayaks

3.0 star property
Vibrant Sterling Lakefront Lodge w/ Kayaks
Waterfront New England House on Wickaboag Lake!
Interior

Waterfront New England House on Wickaboag Lake!

3.0 star property
Waterfront New England House on Wickaboag Lake!
Stunning Sterling Sanctuary: Unwind on the Water!
Interior

Stunning Sterling Sanctuary: Unwind on the Water!

3.0 star property
Stunning Sterling Sanctuary: Unwind on the Water!
Beach Front Stay on Fully Recreational Lake at the base of Wachusett Mountain
Fridge, microwave, oven, stovetop

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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free