Photo by Dawn Madden

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Compare 35 Cottages in Ashby with updated reviews, rates, and availability.

Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Mt. Monadnock from the shore
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
10.0 out of 10, Exceptional, (28)
"This pearl of an oasis is on Pearly Pond with a breath-taking view of Mount Watchusett. Nestled in a quiet cove, it is still close to local amenities, trails and restaurants. The cabin has everything a person could image to bring on vacation such as nice cookware, beach towels, and games. The home boasts a lovely screened in porch and a beautiful dock with canoe and kayak. We highly recommend this cabin. Gary and Linda are consumate hosts!!"
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Exterior
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
9.4 out of 10, Exceptional, (16)
"Place was pristine, great location on the lake. Beautiful scenery with the mountains, used the kayaks to get around the lake and catch some fish! My son and i caught pickerel, perch, bass, crappies, and pumkinseeds. Quick drive from Boston @ a little over a hour."
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Waterfront Cottage on Scenic Sportsman Pond
154 Acre sportsman's Pond, for fishing & boating. Flat boards to swim off.
Waterfront Cottage on Scenic Sportsman Pond
9.6 out of 10, Exceptional, (41)
"Sportsman's Pond and Blueberry Cottage provided the ideal location for disconnecting from the noise and busyness of every day life. The pond was beautifully serene, without outboard motors, jet skis, etc. The fall colors were gorgeous. The hosts provided every sort of watercraft one might want. I kayaked everyday exploring the shoreline and watching for birds. The cottage was well equipped, the bed was comfortable and an assortment of chairs and couches were available for lounging, viewing the...
Waterfront Cottage on Scenic Sportsman Pond
Cottage on Partridge Pond
Lake
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (16)
"Lovely home with a small dock in a large pond! Kayaks in the back yard. Beautiful looking out to the pond. Very comfortable home. Hosts are very responsive. We would definitely stay here again. Nice job!"
Cottage on Partridge Pond
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
10.0 out of 10, Exceptional, (14)
"The property is lovely. It suited our needs and fully equipped. "
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Exterior
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
Finnish cottage with Sauna on Lake Monomonac
Exterior
Finnish cottage with Sauna on Lake Monomonac
2.0 star property
10.0 out of 10, Exceptional, (9)
"We really enjoyed our stay at this peaceful cottage on the lake. We wanted to enjoy nature, unplug, and do some fishing and this location did not disappoint. Even though it rained it did not deter us from enjoying the dock and fishing. The next night we used the fantastic natural sauna and I swear my skin feels softer. We also used the firepit on site. Jim was an awesome host and easy to communicate with. We did not have any issues and would return in a heartbeat. "
The price is SAR 560
SAR 921 total
includes taxes & fees
20 Nov - 21 Nov
Finnish cottage with Sauna on Lake Monomonac
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Beach
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
9.4 out of 10, Exceptional, (3)
"We loved the lake and the location. Very nice lake. My kids loved swimming, kayaks and paddle boats. Lovely dock with gorgeous sunset. House is very rustic. The stairs are steep and slippery. Could use a handle rail for safety and may not be appropriate for those with small kids or mobility issues. Beds very small. Screened porch room had some defects in the screen and because of this there were lots of bugs. Otherwise comfortable and very fun. Owners responsive and cabin quite cute and...
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself
View from the lake
Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself
9.6 out of 10, Exceptional, (18)
"Our kids said the beds were the most comfortable beds they'd ever slept on, with the coziest blankets. The cabin was warm, cozy, and homey. Host was very nice and communication was timely and helpful. Beautiful view on the lake. Close to all amenities, shopping, and grocery stores."
Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself
Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks
Property grounds
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
Charming Jaffrey Cottage w/ Deck & Grill!
Jaffrey Vacation Rental | 4BR | 1.5BA | 1,800 Sq Ft | Steps Required
Charming Jaffrey Cottage w/ Deck & Grill!
10.0 out of 10, Exceptional, (39)
"Stayed four nights. Perfect weather and the foliage was fabulous.The cottage was ideal for us. Tastefully decorated and everything labeled. Wish we lived closer so we could go again in other seasons."
Charming Jaffrey Cottage w/ Deck & Grill!
Beach & pond Cottage
Terrace/patio
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
Heated pool next to gym, both overlooking the water.
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
Historic Home w/ Modern Updates on < 4 Acres
Exterior
Historic Home w/ Modern Updates on < 4 Acres
3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Cozy Tiny House on Main Street. Fully Renovated.
Most of the Tiny House. Looking out from the bedroom doorway
Cozy Tiny House on Main Street. Fully Renovated.
10.0 out of 10, Exceptional, (4)
"I was in Dublin visiting my daughter who goes to high school here and it was the perfect place for me to stay and she stayed with me two nights. The owner thought of everything you would need. It was super clean and everything looked brand new. Really well decorated. The owner was super helpful and I’m sure I’ll be back before my girl graduates. Highly recommend!"
Cozy Tiny House on Main Street. Fully Renovated.
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
Exterior
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
The Cozy Cottage
Outdoor dining
The Cozy Cottage
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay. The seating outside was lovely!"
The Cozy Cottage
Inviting Summer Village Cottage: Golf Cart & More!
Westford Vacation Rental | 2BR | 1BA | 800 Sq Ft | Steps Required
Inviting Summer Village Cottage: Golf Cart & More!
Inviting Summer Village Cottage: Golf Cart & More!
Charming Jaffrey Cottage w/ Deck & Grill!
Property grounds
Charming Jaffrey Cottage w/ Deck & Grill!
3.0 star property
Charming Jaffrey Cottage w/ Deck & Grill!
Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site
Exterior
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
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 Ashby

Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly
contemporary hilltop house
Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly
10.0 out of 10, Exceptional, (42)
"There were so many great amenities included with this stay. A very modern, energy efficient and health conscious guest house. Our favorite parts were the wood-burning stove, wrap around deck, fully stocked, high-end kitchen, heated towel rack and bathroom floor, and a very remote location. A small-town getaway within an hour's drive of downtown Boston."
The price is SAR 1,127
SAR 2,002 total
includes taxes & fees
17 Nov - 18 Nov
Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly
Charming Waterfront Log Cabin
Exterior
Charming Waterfront Log Cabin
9.4 out of 10, Exceptional, (34)
"Awesome"
Charming Waterfront Log Cabin
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Exterior
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.

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