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Oakham Holiday Rentals

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    £167 Average
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    Don't let other travellers get your favourite Oakham area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 15 Rentals in Oakham
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    The following rentals are within 30 kilometres of Oakham.
    West Brookfield
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Hubbardston
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sterling
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Stone 'n Sky Lodge on an Ancient Stone Landscape1 / 32
    (5)Excellent
    New Salem
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    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...
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    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...
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    Location Information
    New Salem, Massachusetts 01355
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    Belchertown
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Satellite TV
    • Grill
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning 5,000-square-foot Tudor-style vacation rental home sits on 9 acres of professionally landscaped private property, ensuring an unforgettable Massachusetts retreat. Four bedrooms and 2.5 bathrooms comfortably accommodates 8 guests, with additional sleeping arrangements for up to 15 and...
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    Location Information
    Belchertown, Hampshire County 01007
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    West Wing in Country Farmhouse, Private, Romantic1 / 20
    (1)Excellent
    Barre
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    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...
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    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...
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    Location Information
    Barre, Massachusetts 01005
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Worcester
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a split-level house, the entire upper floor is available for rent. I live in the lower floor. These are totally separated units with private entrance each. The back yard is a hidden paradise in the Summer months and it is exclusive for the guests. However, I maintain the swimming pool and...
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    Location Information
    Worcester, Massachusetts 01606
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Brimfield Lakeside Home1 / 23
    (4)Excellent
    Brimfield
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • DVD Player
    • Parking
    • Satellite TV
    • Grill
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2017
    I can't say enough great things about Shannon and Tom and their lake house as well!! My family and I so enjoyed our stay there! Attention to every detail made our vacation so...
    Reviewed 22 May 2017
    My mom and I went to the lake house on a mother daughter vacation to the Brimfield flea market. It felt like we went from our homes to a home on a lake and we instantly felt...
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    About this property
    Newly renovated year round cottage located in a quiet cove on Little Alum Pond in Brimfield, Massachusetts only minutes from downtown Sturbridge and the Brimfield Flea Market. Enjoy the serenity of being on this spring fed lake, where you can swim, fish and boat...quiet, peaceful and relaxing! (All...
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    Location Information
    Brimfield, Massachusetts 01010
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Non smoking In-Laws Quater1 / 27
    (1)Excellent
    Worcester
    1 Bedroom, Sleeps 1 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 April 2014
    Beautiful, Zen like home, gorgeous gardens, peaceful, huge projector tv, state of art kitchen, hospitable hosts, quiet, exceptional value, beautiful decor. Perfect rental, esp...
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    About this property
    This is a very nice and clean in-laws-quarters apartment with a private entrance on the first floor of our home. It has full bathroom, laundry room, (available with a minimum of 2 weeks stay) small living room, fully furnished eat in kitchen with dishwasher, electrical stove, microwave,...
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    Location Information
    Worcester, Massachusetts 01606
    Condo/Apartment - 1 Bedroom, Sleeps 1
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    Southbridge
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The space is a 1200 square foot apartment that has a lot of charisma and charm. The lot is the largest in the street with many trees and flowering trees in the early spring to summer. The apartment is air conditioned in the summer and heated in the winter. Bath towels and basic personal care items...
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    Location Information
    Southbridge, Massachusetts 01550
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Artist get away1 / 41
    (3)Very good
    Southbridge
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Porch
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Washer
    • Secure Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2016
    Tom's apartment was everything you want in a vacation rental: bright, clean, comfortable, and relaxing. Plenty of space, beautiful and high-quality furniture, just all-around...
    Reviewed 30 August 2015
    Why stay in a hotel when you can have a whole apartment for the same or less money. This one will fill all your needs. Clean, comfortable, close to area attractions &amp...
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    About this property
    Located on an old and quite street,Roger Street is situated in front of a very nice brook. Of the right day you can see great blue heron fly a few feet above the water. This 1100 SF 2 bed room apt has a very warm and artsy flair furnished in traditional and antique furniture. Watch TV or a DVD....
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    Location Information
    Southbridge, Massachusetts 01550
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Victorian House Apartment1 / 5
    (1)Excellent
    Clinton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Grill
    • Satellite TV
    • Hot Tub
    • Internet Access
    • Washer
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2016
    A piece of New England history. Beautifully maintained victorian house with large rooms, period restored original flooring, door archways and more. Nice garden area with plenty...
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    About this property
    Victorian House Apartment,three bedrooms,two bathrooms,Large Living Room,Dining Room,Kitchen and Front Porch.All hardwood floors,beautiful gardens surrounding house.Bright,light living spaces very comfortable.All bedrooms are very spacious with lots of windows.Rentals start at $150.00 for the one...
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    Location Information
    Clinton, Massachusetts 01510
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Belchertown
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful turn-of-the-century Victorian is the former rectory to a beautiful old church that is now an artist studio (The Artist Common - available for rent separately). It is secluded a top a hill on 4 1/2 acres and has soaring ceilings, period details, modern kitchen and 2 1/2 bathrooms. You...
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    Location Information
    Belchertown, Hampshire County 01007
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    Big Sky Hilltop Sunset Room1 / 10
    (1)Excellent
    Belchertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2016
    What a lovely opportunity to meet these two gracious hosts. If/when I return to Amherst theirs will be the first lodging I look into. Morning coffee on the back deck watching...
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    About this property
    Only 10 minutes from Amherst Center but almost 1000 feet above it and with a view for 60 miles, BigSkyHilltop is convenient to the 5 colleges, but a country gettaway looking out over the pastures of our neighbor's alpacas and donkeys with the forests and the Holyoke Hills beyond. Comfortable,...
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    Location Information
    Belchertown, Hampshire County 01007
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    BigSkyHilltop Westerly Room1 / 8
    (1)Excellent
    Belchertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 October 2016
    Our second two-night stay at Big Sky Hill Top was just as great as the first! This really is a BnB style rental: a great breakfast was included. They really go out of their way...
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    About this property
    Only 10 minutes from Amherst Center but almost 1000 feet above it and with a view for 60 miles, BigSkyHilltop is convenient to the 5 colleges, but a country gettaway looking out over the pastures of our neighbor's alpacas and donkeys with the forests and the Holyoke Hills beyond. Comfortable,...
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    Location Information
    Belchertown, Hampshire County 01007
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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