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 Homes and Apartments Oakham, MA and nearby

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.
dd/mm/yyyy dd/mm/yyyy
    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}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $287 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Oakham area holiday rental. You're so close to securing your perfect getaway. Book today.

    The following rentals are within 40 kilometres of Oakham, Massachusetts.

    1 / 5
    5 of 5 bubbles (1) Excellent
    Clinton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 23
    5 of 5 bubbles (2) Excellent
    Brimfield
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 32
    5 of 5 bubbles (3) Excellent
    New Salem
    4 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 13
    Worcester
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    My apartment is recently renovated and very clean. You will feel very comfortable staying here. Breakfast and parking included. Everything you need for a wonderful stay is here. Good location in quiet street not far from highway, DCU and colleges. Wifi avialable. I have experience working in a... View all property information
    Location Information
    Worcester, Massachusetts 01605
    1 / 23
    West Brookfield
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Waterfront
    • Air Conditioning
    • Outdoor Dining Area
    • Grill
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    1 / 20
    5 of 5 bubbles (1) Excellent
    Barre
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    5 of 5 bubbles 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 you...
    See all reviews
    1 / 37
    5 of 5 bubbles (16) Excellent
    Ashburnham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    5 of 5 bubbles Reviewed 1 August 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...
    5 of 5 bubbles 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
    1 / 10
    5 of 5 bubbles (1) Excellent
    Belchertown
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    5 of 5 bubbles Reviewed 14 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
    1 / 8
    5 of 5 bubbles (1) Excellent
    Belchertown
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    5 of 5 bubbles Reviewed 27 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 to...
    See all reviews
    1 / 23
    4.5 of 5 bubbles (3) Very good
    Southbridge
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Air Conditioning
    • DVD Player
    • Porch
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    5 of 5 bubbles Reviewed 14 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...
    4 of 5 bubbles 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 & shopping...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 7
    Sterling
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Grill
    • Washer
    • Skiing: Property Is...
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 21
    Belchertown
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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