We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Winchendon Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $246 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Winchendon area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 15 Rentals in Winchendon
    Sort by:
    Default
    The following rentals are within 30 kilometres of Winchendon.
    Winchester, NH
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Troy, NH
    3 Bedrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Fitzwilliam, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Winchester, NH
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Stunning Lakefront home on crystal clear, sandy bottomed, 110 acre Forest Lake at the junction of NH,VT,& MA will be your long awaited retreat in the whispering pines, shimmering lakes, and beautiful foliage of New Hampshire. Bring the kids & dogs or just enjoy by yourselves. <BR>The Great room...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Richmond, NH
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Balcony
    • Mountain Views
    • Wi-Fi
    • Washer
    • Patio
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This historic home on 24 wooded acres in New Hampshire about 20 minutes south of Keene was built in 1774 and occupied by a Revolutionary War family. Additions over the centuries make it a rich experience of history, nature, fireplaces and wood-burning stoves, rich furnishings, and modern amenities!...
    View all property information
    Location Information
    Richmond, New Hampshire 03470
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Hubbardston
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Grill
    • Balcony
    • Patio
    • Mountain Views
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy cabin home located on pond. 1.5 bedrooms. 1.5 bathrooms. 1/2 kitchen in main house , full kitchen is located in outbuilding. kayaks, paddleboat, paddle board all on site. internet , cable tv, and xbox 1. this is a rustic very private setting. if you are looking to get away from it all this is...
    View all property information
    Location Information
    Hubbardston, Massachusetts 01452
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Jaffrey, NH
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • Porch
    • Patio
    • Grill
    • Mountain Views
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1) Beautiful historic property, originally an early 1800's tavern with a rich history as a working farm, seasonal vacation home, inn and year round residence. Property sits at the base of Mt. Monadnock with beautiful mountain and pastoral views. Our street address is Mountain Rd., 2) One of...
    View all property information
    Location Information
    Jaffrey, New Hampshire 034526002
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
    Make Enquiry
    1830 Private Storybook Country Home on 78 Acres1 / 37
    (16)Excellent
    Ashburnham
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2016
    We stayed at the Elijah Haven Homeplace for 1 week and wish we never had to leave. Between the historic house and the beautiful grounds it was the perfect spot for our family...
    Reviewed 1 August 2015
    We spent a week at John and Scott's incredible Home Haven...woke with the sun to walk the gorgeous property each morning... Joined by turkeys, chipmunks and porcupine.. Up the...
    See all reviews
    About this property
    Summer vacation in the hills of Central MA just west of Boston. Make memories "someplace different". We're closer to Boston than the Berkshires and with many fewer traffic jams than the Cape and Islands. 1830 Elijah Haven Homeplace is a very sweet, private and quintessential New England country...
    View all property information
    Location Information
    Ashburnham, Massachusetts 01430
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Beautiful Lake Side Getaway, Quiet, and Peaceful1 / 21
    (4)Excellent
    Winchester, NH
    2 Bedrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2014
    Great off the beaten track place to stay yet only 20 minutes from Keene. Bill and Sandie very gracious hosts both before and during your stay. Accommodations very modern. We...
    Reviewed 12 July 2014
    My fiancé and another couple stayed here for a few days in May. It was absolutely beautiful and exactly what we were looking for! My fiancé and I are avid "outdoors...
    See all reviews
    About this property
    2 Bedrooms, 1 bath, sleeps 6. Private beach, dock, raft, rowboat, canoe, 5 Kayaks, or launch your boat. Cable TV, high speed internet, WIFI, 42' flat screen internet TV. Sleeps 6 - two bedrooms - One with Queen Bed, one with two single beds (can be made into Queen), and a full size pullout couch in...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Condo/Apartment - 2 Bedrooms, Sleeps 6
    Make Enquiry
    Cozy Cabin at the base of Mt Monadnock1 / 13
    (3)Very good
    Jaffrey, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Wi-Fi
    • Central Heating
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2016
    This place has place was nice and cozy. We were able to use the fireplace and stay warm in the month of February. We used the Porch a lot and enjoyed the sunset view on the east...
    Reviewed 6 July 2015
    A lovely cabin/home. Very clean and well-appointed with the basics. Helpful instructions about the home as well as area info--owners clearly have comfort of their guests in mind...
    See all reviews
    About this property
    Nestled at the base of the mountain, sits our log cabin. A quiet, country area with neighbors within walking distance but not within view. Perennial flowers and trees surround the property with a brook for a backdrop, as well as an expanse of lawn for yard games and campfire. Inside you'll...
    View all property information
    Location Information
    Jaffrey, New Hampshire 03452
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Save time - get the best Winchendon rentals sent straight to your email!
    Get the List
    Stone 'n Sky Lodge on an Ancient Stone Landscape1 / 32
    (5)Excellent
    New Salem
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Grill
    • Porch
    • Mountain Views
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Great accomodations for a whole bunch of people. Four bedrooms with beds for 10 PLUS additional mattresses for the kids. Fresh eggs and coffee from the hosts were a nice treat...
    Reviewed 11 June 2017
    We visited New Salem for 5 days in the end of May. We were welcomed by a cheerful Sarah carrying a carton of organic eggs from her farm next door. Obviously a good start! For a...
    See all reviews
    About this property
    Gorgeous, spacious, red-oak post and beam home on 11.25 acres abutting 2,700 acre Wildlife Preserve. 3-5 bedroom, 3 bath, 2600 sq ft, fully furnished and appointed, Stone 'n Sky Lodge offers extraordinary privacy and local convenience. Located on a paved, town-maintained, dead-end road surrounded...
    View all property information
    Location Information
    New Salem, Massachusetts 01355
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Enquiry
    Lakefront Cottage1 / 24
    (3)Very good
    Rindge, NH
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Waterfront
    • Satellite TV
    • Parking
    • Outdoor Dining Area
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2016
    First, the owner is wonderful. Second, the cottage is right on beautiful, quiet Pearly Lake. I was here for 4 weeks in July and the lake was always peaceful. You can swim to...
    Reviewed 15 October 2015
    My husband & I had the pleasure of staying in this sweet cabin with our three kids (five, three and one). We absolutely loved our stay! The sun sparkling on the lake each...
    See all reviews
    About this property
    Here is the perfect location for your family vacation or a couple's getaway. Pearly Pond offers all of your favorite outdoor activities. Choose from swimming, canoeing (kayaking), hiking, mountain biking or fishing. If you're more into relaxing, just stretch out on the deck with your favorite...
    View all property information
    Location Information
    Rindge, New Hampshire 03461
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Peterborough, NH
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Balcony
    • Satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An easy one mile walk from downtown Peterborough (sidewalks all the way) with all its fantastic shopping, dining, parks, and quintessential New England charm. This recently renovated two bedroom riverside cottage sleeps four people. With its updated kitchen, spacious living room, screened-in porch,...
    View all property information
    Location Information
    Peterborough, New Hampshire 03458
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    West Wing in Country Farmhouse, Private, Romantic1 / 20
    (1)Excellent
    Barre
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2014
    This was our second stay at Maple Grove Farm. The second apartment we stayed in this year was just as nice as the first one we stayed in two years ago. Rebecca and Dot make...
    See all reviews
    About this property
    Come stay in an apartment in the Maple Grove Farmhouse built in 1823. The house is surrounded by 140 acres of fields and woods for great hiking. Take a walk to the beaver pond that sits at the foot of the hill; if you get up early enough you will see the beavers. Swing under the huge maples or walk...
    View all property information
    Location Information
    Barre, Massachusetts 01005
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Pet-friendly private, peaceful, pond-front home1 / 16
    (1)Very good
    Fitzwilliam, NH
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Patio
    • Mountain Views
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2016
    We wanted to get our city dogs out to the country where they could be off leash.This being the last house on the road helped us to feel comfortable letting the dogs run.We...
    See all reviews
    About this property
    (Please note that the FlipKey 'per night' quote is for a weekly rental and their "Ready to book?" quote does not include the security deposit amount.) We book Sunday to Sunday. If we are not booked within three weeks of a date, then we open up to partial week rentals. Our minimal rental is 2...
    View all property information
    Location Information
    Fitzwilliam, New Hampshire 03447
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property
    Owner log in