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.

Holiday Rentals in Oakham

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
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
    €192 Average
    |||
    |||
    €0€1,000+
    Suitability
    More filters
    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
    Sort by:
    Default
    The following rentals are within 40 kilometers of Oakham.
    Brimfield Lakeside Home1 / 23
    (3)Excellent
    Brimfield
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Non smoking In-Laws Quater1 / 15
    (1)Excellent
    Worcester
    1 Bedroom, Sleeps 1 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Victorian House Apartment1 / 5
    (1)Excellent
    Clinton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Stone 'n Sky Lodge on an Ancient Stone Landscape1 / 32
    (4)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 2 weeks ago
    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...
    Reviewed 17 October 2014
    The house was clean, had three bedrooms with many beds, and had an amazing back yard with frog pond and patio with two barbeque grills. Coffee was left for us to drink in the...
    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
    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
    Big Sky Hilltop Sunset Room1 / 10
    (1)Excellent
    Belchertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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,...
    View all property information
    Location Information
    Belchertown, Hampshire County 01007
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    West Brookfield
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Waterfront
    • Air Conditioning
    • Outdoor Dining Area
    • Grill
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Prepare for the perfect New England weekend away when you book this Massachusetts lakeside retreat! Bring friends, family or both and relish in the charming country-style home that awaits.   With 4 full bedrooms, this is the perfect nest for families or groups of friends traveling together who...
    View all property information
    Location Information
    West Brookfield, Massachusetts 01585
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Enquiry
    Worcester
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Eight Hycrest Drive is a spacious, clean and very well maintained 3BR beautiful zen home, on a quiet street in a nice neighborhood, Burncoat, in Worcester. Eight Hycrest Drive is beautifully decorated and has plenty of light. Its kitchen is big, with modern appliances, granite countertops and...
    View all property information
    Location Information
    Worcester, Massachusetts 01606
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Artist get away1 / 41
    (3)Very good
    Southbridge
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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....
    View all property information
    Location Information
    Southbridge, Massachusetts 01550
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Sterling
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Grill
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful secluded modern home on a private lake with beautiful lake views from every window, kayaks/paddleboards/boats you can use, outdoor fire pit, fishing, two docks. Close to lots of activities year-round. House has linens and fresh sheets. Kitchen is fully stocked with dishes, pots, pans,...
    View all property information
    Location Information
    Sterling, Massachusetts 01564
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    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
    BigSkyHilltop Westerly Room1 / 8
    (1)Excellent
    Belchertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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,...
    View all property information
    Location Information
    Belchertown, Hampshire County 01007
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Southbridge
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Southbridge, Massachusetts 01550
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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
    Belchertown
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Belchertown, Hampshire County 01007
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Enquiry
    List your property
    Owner log in