Search Cottages in Oakham

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Compare 19 Cottages in Oakham with updated reviews, rates, and availability.

Beautiful & Historic Cottage, Steps to Elm Park
2.5 star property
10.0 out of 10, Exceptional, (1)
"Perfect time and my chocolate lab loved it! The owners couldn’t have been any nicer. Highly recommend!"
Beautiful & Historic Cottage, Steps to Elm Park
Trainmaster's Inn - Caboose
9.4 out of 10, Exceptional, (3)
"Husband is a railfan he was at the tracks several times a day"
Trainmaster's Inn - Caboose
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (15)
"This place was perfect for a family vacation with kids under 6. Todd had everything to make it fun for them to spend most of the day in the water, which was really easy for kids to get into with the dock and a shallow entry. The kayaks were so fun and had kid sized life vests. I also really appreciate how responsive Todd was throughout the stay. Highly recommend! "
Cottage on Partridge Pond
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
9.4 out of 10, Exceptional, (13)
"the property was beautiful only thing i was upset about was the light not working in the kitchen and the back porch also bugs were a huge problem in the house like beetles and little pincher things spiders and ect also my kid got a tick as well other than that it was a beautiful place peaceful a beautiful stay"
The price is SAR 750
SAR 1,638 total
includes taxes & fees
15 Oct - 16 Oct
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
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
Sun-dappled Retreat - Walk to Wickaboag Lake!
3.0 star property
Sun-dappled Retreat - Walk to Wickaboag Lake!
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
Worcester Home on Indian Lake w/ Shared Boat Dock!
3.0 star property
Worcester Home on Indian Lake w/ Shared Boat Dock!
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!
Spacious Oxford Home w/ Pool - 4 Mi to Lake!
3.0 star property
Spacious Oxford Home w/ Pool - 4 Mi to Lake!
Vibrant Sterling Lakefront Lodge w/ Kayaks
3.0 star property
Vibrant Sterling Lakefront Lodge w/ Kayaks
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
Stunning Sterling Sanctuary: Unwind on the Water!
3.0 star property
Stunning Sterling Sanctuary: Unwind on the Water!
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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.
9.6 out of 10, Exceptional, (18)
"My son and I were in town for sports and it was great to have a home base. It's clean, cozy, had everything we needed, and good location to town and highways. (We stayed on second floor so there is a full flight of stairs to get in.) Host is great and super responsive. 2 Quick notes: offers a hot plate rather than a full stove and low ceilings for my 6'2" son, but overall we had a great visit and would go back if in the area again."
The price is SAR 476
SAR 964 total
includes taxes & fees
30 Sep - 1 Oct
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, (175)
"Beautiful property with easy access to the lake. The three of us were comfortable with the home. The house is in a hilly neighborhood which would not be ideal for older adult walkers, but was fine for us. There was an unusually strong "garlicky" smell in the house that could use some scented or odor neutralizing candles. I don't know if it was from cooking, the floral shop or a natural insect repellant. Just worthy of note. A dehumidifier was in one of the bedrooms. Window air...
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Large relaxing house in 25 acres of private woods with lake access.
10.0 out of 10, Exceptional, (14)
"Jim’s home was the perfect resting place & backdrop to my eldest sons wedding! The home provided space for all my immediate family members who traveled from Hawaii, Oregon, Florida, Vermont & New Hampshire. It’s was a quiet and peaceful retreat from all the hustle & bustle of a larger than life wedding weekend. The home has a large and well equipped kitchen, comfortable beds, and beautiful surroundings! We would def stay here again—thank you Jim for sharing this wonderful space with us!"
Large relaxing house in 25 acres of private woods with lake access.
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.