Holiday Homes in Winchendon

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Featured Holiday Homes in Winchendon

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Exterior
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
9.8 out of 10, Exceptional, (6)
"We stayed for a lacrosse tournament in Devens MA. Only 20 minutes away and the house was perfect!"
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Lovely 3-bedroom City Escape
Property grounds
Lovely 3-bedroom City Escape
9.8 out of 10, Exceptional, (16)
"One of the best places I’ve stayed! My father was raised in Barre and we often have to stay in Gardner when we visit. It was amazing to not have to drive 20+ minutes to get to my cousins farm. The house feels like home. The beds were all comfortable. It was nice to be able to spread out and have enough space for everyone to relax. Couldn’t have asked for a better situation or host! I will definitely be booking again."
Lovely 3-bedroom City Escape
Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!
Property grounds
Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!
10.0 out of 10, Exceptional, (67)
"Stayed over for a brief visit to take my elderly mother away to get out of the house as she loves to be on or near the water whenever possible. Great clean space tranquil and pleasant grounds."
Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!
Quiet private pond getaway
Property grounds
Quiet private pond getaway
9.8 out of 10, Exceptional, (6)
"This bungalow was perfect for our weekend away! Very clean and the dock on the pond was the perfect touch. the property manager responded to my question super quickly as well. We would love to visit again soon! :) "
Quiet private pond getaway
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, desk, iron/ironing board, Internet
Historic Home w/ Modern Updates on < 4 Acres
10.0 out of 10, Exceptional, (5)
"The property was awesome! Old, quaint and brought memories back of our grandparents homes…Family sat around table and enjoyed shared memories"
Historic Home w/ Modern Updates on < 4 Acres
LAKE FRONT: Cozy 4-bedroom lake camp with WiFi and an outdoor firepit!
Property grounds
LAKE FRONT: Cozy 4-bedroom lake camp with WiFi and an outdoor firepit!
2.0 star property
9.0 out of 10, Wonderful, (2)
"Cozy lake cottage that offers the rustic feel with cozy accommodations. If you are wanting luxury this is not for you. This ideal for those who appreciate lake life while offering northern Massachusetts vibes in local towns. We were there for a disc golf tournament at maple hill. Location was great to fit in a few other courses as well. "
LAKE FRONT: Cozy 4-bedroom lake camp with WiFi and an outdoor firepit!
Charming Waterfront Log Cabin
Interior
Charming Waterfront Log Cabin
9.4 out of 10, Exceptional, (34)
"Awesome"
The price is NZ$583
includes taxes & fees
21 Oct - 22 Oct
Charming Waterfront Log Cabin
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
9.8 out of 10, Exceptional, (13)
"Had a great time at this property, well perfectly situated at the center of our interest areas in New Hampshire."
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
Exterior
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
9.8 out of 10, Exceptional, (81)
"Plenty of room. Nice area. Would return again."
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Lake
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."
The price is NZ$800
includes taxes & fees
27 Sept - 28 Sept
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
VERY LUXURIOUS QUIET AND PEACEFUL APARTMENT ..PRIVATE ENTRANCE
Exterior
VERY LUXURIOUS QUIET AND PEACEFUL APARTMENT ..PRIVATE ENTRANCE
8.0 out of 10, Very good, (4)
"the hosts were fantastic! They were so welcoming and went out of their way to be take care of our every need even during the Christmas holiday. We were so thankful for how dog friendly they were and the neighborhood was perfect for dog walking. I would definitely stay here again."
The price is NZ$561
includes taxes & fees
21 Oct - 22 Oct
VERY LUXURIOUS QUIET AND PEACEFUL APARTMENT ..PRIVATE ENTRANCE
Downtown Hot Tub Escape
Property grounds
Downtown Hot Tub Escape
9.4 out of 10, Exceptional, (8)
"Very nice house brand new appliances. Water pressure was very strong and got nice and hot for showers. Everything was labeled easy to find the host Rebecca was would respond in minutes if I had a question highly recommend this place"
The price is NZ$557
includes taxes & fees
23 Oct - 24 Oct
Downtown Hot Tub Escape
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
Fridge, microwave, oven, stovetop
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Exterior
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
10.0 out of 10, Exceptional, (63)
"Plenty of room for everyone, bathrooms A+, especially with that many people. 8 total, ages from 24-85. Perfect for everyone "
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Beautiful Lakefront home - perfect getaway for every season!
Property grounds
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!
Waterfont log home nestled in the pines
Property grounds
Waterfont log home nestled in the pines
10.0 out of 10, Exceptional, (48)
"The cabin was perfect for my friends and I to get away from the city for a few nights. Super cozy and the dock was great. We had a lot of fun paddling around the lake!"
Waterfont log home nestled in the pines
Private Field House - Spacious 4 Bedroom Home
Fridge, microwave, oven, stovetop
Private Field House - Spacious 4 Bedroom Home
10.0 out of 10, Exceptional, (12)
"We had a wonderful stay at the Dublin field house. Brie was an attentive host answering questions about local dining and offering to pick up groceries ahead of our arrival. Our party arrived in stages so knowing there were already snacks in the fridge was a huge relief. On our way home we were already talking about when we could stay again!"
Private Field House - Spacious 4 Bedroom Home
Nestled on the edge of the woods near Mount Monadnock
Fridge, microwave, oven, stovetop
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
Copley’s Guest House on Lake Monomonac
Interior
Copley’s Guest House on Lake Monomonac
10.0 out of 10, Exceptional, (2)
"Great one bedroom on the lake with wonderful views"
Copley’s Guest House on Lake Monomonac
Meadow House at Powder Mill Pond - a nature lover's paradise
Property grounds
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
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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 Winchendon

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Interior
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
Interior
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 in ground pool, Epic views of Lake Monomonac
Fridge, microwave, oven, stovetop
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
Amazing Lakefront property, Private in ground pool, Epic views of 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.