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Compare 32 Cottages in Sterling 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
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
10.0 out of 10, Exceptional, (4)
"This property was great. Wonderfully modern lake front home. Recommend renting the pontoon to fish for larger fish. Kayaks, Paddleboards, great restaurants and sauna. Picture perfect scenery. "
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Beautiful Modern Cottage with Sauna on Lake Monomonac
2.0 star property
10.0 out of 10, Exceptional, (1)
"This was our 2nd stay with the host. Everything was perfect and relaxing. "
The price is AED 731
AED 1,235 total
includes taxes & fees
29 Sep - 30 Sep
Beautiful Modern Cottage with Sauna on Lake Monomonac
Finnish cottage with Sauna on Lake Monomonac
2.0 star property
10.0 out of 10, Exceptional, (7)
"We live in mass and just wanted to take a weekend to get away we picked the cutest little place and we are so happy we picked this one !! The house was just perfect !! Clean !! Next to the water just what we wanted !! Bonus is that Jim welcomed us like we were family I would recommend any of the 3 little homes his family rents out they are a beautiful family memory !! Thank you it's just what we wanted !! "
The price is AED 731
AED 1,128 total
includes taxes & fees
21 Oct - 22 Oct
Finnish cottage with Sauna on Lake Monomonac
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
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 AED 735
AED 1,604 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
Beach & pond Cottage
9.6 out of 10, Exceptional, (5)
"The cottage was well laid-out for a small to medium size family to stay. Golf cart was great for taking small children to nearby water features (swimming pools and lake). Other visitors and local residents were very friendly and courteous. Perfect place for a week away from hectic city life."
Beach & pond Cottage
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
10.0 out of 10, Exceptional, (3)
"We stayed here for 5 weeks. I had no idea when I booked it how amazing it would be. My kids say it was the best summer ever. The cottage is so cute. The location is amazing and all the amenities are amazing. They cottage community has so many activities going all the time, the beach and lake are so fun with a dock you can swim to, there is a restaurant on the weekends, riding the gold cart around, the swimming pool… I can’t say enough good about this place! I wish I owned one. Don’t hesitate to...
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
10.0 out of 10, Exceptional, (2)
"Family reunion at our favorite summer place ."
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
Enchanted Cottage on 5 Acres
Enchanted Cottage on 5 Acres
Inviting Summer Village Cottage: Golf Cart & More!
Inviting Summer Village Cottage: Golf Cart & More!
Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site
2.0 star property
10.0 out of 10, Exceptional, (1)
"My wife literally did not want to leave John's cottage at Summer Village. John updated and his wife tastefully decorated their cottage and thought of everything including spices, toiletries, swim toys and a fully stocked kitchen allowing for great home cooked meals. The location is very quiet and private abutting a nature preserve and the neighbors were friendly and welcoming. We swam in the pool and played on the beach every day. John promptly answered any questions we had and offered...
Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site
Classic Waterfront Home on Lake Maspenock w/ Grill
3.0 star property
Classic Waterfront Home on Lake Maspenock w/ Grill
Waterfront Cottage in Summer Village w/ Grill
2.5 star property
Waterfront Cottage in Summer Village w/ Grill
Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods
Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods
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!
Beautiful waterview and water access from adorable cottage
Beautiful waterview and water access from adorable cottage
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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 Sterling

Vibrant Sterling Lakefront Lodge w/ Kayaks
10.0 out of 10, Exceptional, (15)
"Beautiful location. The house is very comfortable with updated everything. I enjoyed the lovely art work and interesting decor. Close to a charming town with good restaurants. Very enjoyable stay."
Vibrant Sterling Lakefront Lodge w/ Kayaks
Residences at Solomon Pond
3.5 star property
8.0 out of 10, Very Good, (124)
"The location was good"
The price is AED 426
AED 476 total
includes taxes & fees
1 Oct - 2 Oct
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
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.