Vacation rentals in Oakham

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Top-rated vacation rentals in Oakham

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Top guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 204 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Guest favorite

Guest suite in Worcester

4.89 out of 5 average rating, 449 reviews

Private Suite with separate entrance in Worcester

The suite allows maximum of two pets per reservation for $50 per a pet. Our guests privacy starts from check in to check out with private entrance. The living room has mini library for guests, a 65 inch smart TV with high speed Internet and complimentary YouTubeTV local channels. The suite has a mini kitchen with mini refrigerator, freezer, microwave, air fryer, and coffee maker. It also has stocked cabinet utensils, cleaning supplies, linen closet and electric pump air mattress if necessary.

Top guest favorite

Guest suite in Hubbardston

4.99 out of 5 average rating, 132 reviews

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Your home away from home is a spacious & newly renovated basement/in-law apartment (approx 1100 sq feet) located below the main house, with its own private entrance, dedicated parking & in walkable neighborhood. The unit has a bathroom, full kitchen, living room & bedroom w/queen bed & extra tv. Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots and lakes. 10 minutes from route 2 and 15 minutes from Mt Wachusetts.

Top guest favorite

Cottage in Spencer

5 out of 5 average rating, 57 reviews

CK Cottage | Cozy Cottage on a Peaceful Pond

Your home away from home - a charming and cozy cottage nestled in a serene, convenient location! Immerse yourself in the tranquil ambiance of this inviting home, with modern amenities and captivating views. All within minutes of what Worcester county has to offer! Perfect for holiday trips, peaceful vacations, weddings, bonfires, BBQs, picnics - a picturesque getaway tailored to your every need. Explore delicious restaurants, breweries, wineries, state parks, and much more during your stay.

Guest favorite

Apartment in Fitchburg

4.93 out of 5 average rating, 82 reviews

The Nest - Private Rental, Full Kitchen

Welcome! Walk up the stairs and into your comfortable space for one or two. Your private living space includes a large, light-filled bedroom that looks out onto the treed yard open to the eat-in kitchen. Suitable for short-term or long-term stays. We are located in a quiet, multi-cultural working class neighborhood, convenient to highway access. Close to Fitchburg State University, Leominster, Wachusett Mountain. This can also be rented as a two room suite: airbnb.com/h/thnest

Top guest favorite

Home in Oakham

5 out of 5 average rating, 173 reviews

Lovely & Peaceful Waterfront Vacation Retreat

Come enjoy this unique & beautiful retreat home, set on 50 acres of wooded land, with a breath-taking view over a 2 mile long, 190-acre body of water, & no houses in sight! Wonderful in any season. Peaceful, healing haven, & great get-away spot for a romantic weekend or family vacation. Perfect for swimming, boating, fishing, hiking, & cross-country skiing--or just relaxing in a hammock, on the deck, or in a bedroom overlooking the water. Youtube Video: Fred's Place, James Crowther

Superhost

Camper/RV in Hubbardston

4.73 out of 5 average rating, 44 reviews

Mom's Doe Haven

Get away from it all when you stay under the stars. Mom's Doe Haven is a 2 bedroom trailer with living room, kitchen , bathroom walk in shower & full porch. Fire pit & gas grill ..all in the middle of the woods. Situated in a small private campground with indoor pool, pond stocked with trout & hiking trails. Connected to Town Forest with trails for hiking. biking & horseback riding. No wi-fi & cell phone service is very spotty. But plenty of fresh air & sounds of nature!

Superhost

Apartment in Gardner

4.78 out of 5 average rating, 32 reviews

Main Street Sanctuary - Cozy, Whimsical Workspace

Cozy Urban Retreat: A snug studio with warm wood interiors and charming decor—your ideal spot to unwind or work in peace. Prime Location: Nestled on Main Street, stroll to tasty restaurants and quirky shops. Enjoy free parking and laundry steps away. Your Space: 300 sq ft studio with a comfy bed, sofa, desk, big walk-in closet, and private ensuite bath. Essentials: Mini-fridge, microwave, kettle, kitchenware, fresh linens, and easy keycode check-in await you.

Guest favorite

Home in Ware

4.94 out of 5 average rating, 131 reviews

Entire 1-st Floor Apt & Specials for 3+ Stays

Comfy, Cozy & Centrally Located place packed with all you need to relax and enjoy your stay. It is a short drive to Amherst, Brimfield Antique Show, Old Sturbridge Village, and local breweries. Restaurants, shopping & grocery such as Mexicaly, Walmart, McDonald's, DD, Subway, Taco Bell, BigY, Domino and etc are all within a 1-3 min walk/drive. If the need arises, please ask for help, I live next house. Please ask if you are looking for a long-term rental. ThankYou

Top guest favorite

Guesthouse in Westminster

4.98 out of 5 average rating, 408 reviews

Guest House - 4 miles from Wachusett Mt.

Welcome to a cozy, newly renovated semi-attached in-law unit! Nestled in a peaceful neighborhood, you’ll be just a short walk from the town center and only a 10-minute drive to the scenic Mount Wachusett. With easy access to Route 2, it’s the ideal base for your adventures. Enjoy the privacy of your own entrance and two dedicated parking spaces. Whether you’re here for a weekend getaway or a longer stay, we’re sure you’ll enjoy your time in this inviting space!

Guest favorite

Barn in Holden

4.89 out of 5 average rating, 468 reviews

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Guest favorite