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Compare 41 Vacation Homes in Winchendon with updated reviews, rates, and availability.

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (36)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

10.0 out of 10, Exceptional, (12)
"We had a great time. The house was very nice and clean. The lake was really lovely for boating and swimming."
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Waterfont log home nestled in the pines

10.0 out of 10, Exceptional, (49)
"Beautiful secluded location. Quiet neighborhood right on the lake. Wonderful to go down to the dock in the morning and watch the lake come alive with a good cup of coffee. Plenty of room for the family. The log cabin interior was very cozy, clean and inviting. Kitchen had everything needed. The kayaks and fishing poles were put to good use. We stayed here to attend a nearby family wedding and it was SOOO much nicer than being in a hotel, having the family all together. Alfred made sure to check...
Waterfont log home nestled in the pines

Lake Adjacent 3-Bedroom Family Home Close to Wachusett Mountain!

9.8 out of 10, Exceptional, (85)
"Home was clean and comfortable. My extended family and I stayed two nights for a wedding in the area and a good time was had by all. No complaints with the accommodations and the hosts communicated well."
Lake Adjacent 3-Bedroom Family Home Close to Wachusett Mountain!

Historic Home w/ Modern Updates on < 4 Acres

10.0 out of 10, Exceptional, (6)
"Stayed here with my brothers and cousins.. had a great time. Close proximity to Royalston Falls and a great hike through the forest "
Historic Home w/ Modern Updates on < 4 Acres

Charming 3-bedroom waterfront house in Harrisville

Charming 3-bedroom waterfront house in Harrisville

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

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

9.8 out of 10, Exceptional, (15)
"Very nice house and property! "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!

10.0 out of 10, Exceptional, (72)
"We had a lovely stay at this beautiful lakeside retreat. The view was incredible, the home was tastefully decorated and extremely clean. You have thought of everything. This is truly a 10 out of 10! Thank you so much for your kindness and wonderful communication. We couldn't have asked for anything better. We had such a wonderful weekend. We are sure that everyone staying in this home will have a wonderful time."
Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (8)
"It's not luxury, but it's 8,437 times better than a hotel. Hung out by the fire pit after work. Nice neighborhood."
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Quiet private pond getaway

9.8 out of 10, Exceptional, (7)
"Quaint setting with much privacy. All ammendaties were met. Cant wait to return. "
Quiet private pond getaway

Downtown Hot Tub Escape

9.4 out of 10, Exceptional, (9)
"Brought my parents and my Brother to this rental - It was a nice place."
The price is AED 731
AED 1,339 total
includes taxes & fees
1 Dec - 2 Dec
Downtown Hot Tub Escape

Lovely 3-bedroom City Escape

9.8 out of 10, Exceptional, (17)
"A couple friends and I stayed for a long weekend to play local disc golf and thoroughly enjoyed our stay. We loved how spacious, comfortable, and clean Christopher's place was and were thankful to each have our own bedroom. Will definitely be back!"
Lovely 3-bedroom City Escape

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

10.0 out of 10, Exceptional, (1)
"Very nice house on lake with great pool area. Close to town, but not too close. Comfortable beds. Co-located and adjacent to other VRBO houses able to accomadate large family gatherings."
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

10.0 out of 10, Exceptional, (64)
"House was large and comfortable with space for everyone. Enjoyed dinners with our group around the dining table. Kitchen is older but works. Played a charades-type game in the living room one evening. Peterborough wonderful for eats, walking and shopping. "
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Beautiful Lakefront home - perfect getaway for every season!

10.0 out of 10, Exceptional, (4)
"We enjoyed our stay at the house. It was clean and the beds were comfortable. The kitchen had all the basics. One thing of note: there is only a countertop toaster oven, not a full size oven. There is a gas cooktop as well. If you plan to cook while there, that will be an important detail. This house has a great view from the living room. We stayed during some very hot days - approaching 90 degrees. There was no air conditioning in the house, but it was still quite comfortable. There seems to be...
Beautiful Lakefront home - perfect getaway for every season!

Private Field House - Spacious 4 Bedroom Home

10.0 out of 10, Exceptional, (15)
"Very nice home, quiet location, and house had everything we needed and more. Property manager timely communicated all necessary information."
Private Field House - Spacious 4 Bedroom Home

Nestled on the edge of the woods near Mount Monadnock

9.4 out of 10, Exceptional, (6)
"House is comfortable and well stocked."
Nestled on the edge of the woods near Mount Monadnock

Magic Lakehouse, Waterfront, Private Beach and Dock - No Cleaning Fee

10.0 out of 10, Exceptional, (1)
"The house is exactly as advertised. Very peaceful and quiet. It has everything a family may need. Highly recommended."
Magic Lakehouse, Waterfront, Private Beach and Dock - No Cleaning Fee

Meadow House at Powder Mill Pond - a nature lover's paradise

10.0 out of 10, Exceptional, (18)
"We rented this piece of paradise for 3 nights and 4 days, so that our family could all be together. Family came from all over to enjoy this weekend (New Hampshire, Dallas, TX and California). The location was amazing, the proximity to the pond for fishing was convenient for sure, and the surrounding area of the property is absolutely beautiful. Everybody in the family loved the property and had a great time. Thank you to the hosts and to their younger son, who was kind enough to take us...
Meadow House at Powder Mill Pond - a nature lover's paradise
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 Winchendon

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

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

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

10.0 out of 10, Exceptional, (1)
"Very nice house on lake with great pool area. Close to town, but not too close. Comfortable beds. Co-located and adjacent to other VRBO houses able to accomadate large family gatherings."
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
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.