Best Vacation Homes in Oakham
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $314/Night
For 7 Nights US $2,195
US $89/Night
For 7 Nights US $623
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $184/Night
For 7 Nights US $1,291
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $281/Night
For 7 Nights US $1,970
129.17 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- View
- Parking
US $158/Night
For 7 Nights US $1,103
3000 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $391/Night
For 7 Nights US $2,734
844 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $318/Night
For 7 Nights US $2,223
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Kitchen
US $292/Night
For 7 Nights US $2,043
Oakham Luxury Rentals
9484 ft²
13 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,202/Night
For 7 Nights US $8,416
247.57 ft²
9 Guests
4 Bedrooms
3 Bathrooms
House
- Balcony/Terrace
- Parking
- Air Conditioner
US $1,003/Night
For 7 Nights US $7,021
1732.99 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- View
- Parking
US $884/Night
For 7 Nights US $6,188
150.69 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $756/Night
For 7 Nights US $5,292
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $735/Night
For 7 Nights US $5,143
14 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $732/Night
For 7 Nights US $5,126
1728 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $702/Night
For 7 Nights US $4,912
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $630/Night
For 7 Nights US $4,408
Oakham Pet Friendly Vacation Rentals
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $372/Night
For 7 Nights US $2,605
10 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $577/Night
For 7 Nights US $4,038
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $251/Night
For 7 Nights US $1,759
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $331/Night
For 7 Nights US $2,314
1250 ft²
8 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Spa
- Fireplace/Heating
- Ocean View
US $324/Night
For 7 Nights US $2,266
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $493/Night
For 7 Nights US $3,453
1700 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $434/Night
For 7 Nights US $3,038
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $273/Night
For 7 Nights US $1,913
Oakham Large Vacation Homes
2500 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $477/Night
For 7 Nights US $3,340
2497.23 ft²
10 Guests
4 Bedrooms
2 Bathrooms
House
- Oceanfront
- Spa
- Fireplace/Heating
US $339/Night
For 7 Nights US $2,373
12 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $550/Night
For 7 Nights US $3,847
2701.74 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Balcony/Terrace
- Breakfast
- Kitchen
US $522/Night
For 7 Nights US $3,654
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $549/Night
For 7 Nights US $3,846
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $614/Night
For 7 Nights US $4,295
1400 ft²
14 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $402/Night
For 7 Nights US $2,812
2400 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Child Friendly
US $330/Night
For 7 Nights US $2,310
Why Choose Rent By Owner for your Oakham Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Oakham
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this region can greatly enhance your experience, as seasonal changes here influence everything from weather to local activities, making it important to plan your stay accordingly for an enjoyable and memorable vacation.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy pleasant weather and longer daylight hours, making it ideal for outdoor activities in the region's scenic surroundings.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Early Fall (September to October)
This season offers mild temperatures and beautiful fall foliage, providing a charming backdrop for your stay in the area.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter months bring colder temperatures and potential snowfall, perfect if you seek a quiet retreat or winter sports experiences nearby.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
Late Fall to Early Winter (November)
As the region transitions into winter, fewer visitors arrive, offering a more peaceful escape amidst the crisp autumn scenery fading away.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Oakham
How to Book Your Oakham Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Oakham
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for meals surrounded by natural beauty in the area.
- Relax by a private or shared swimming pool, ideal for warm-weather enjoyment here.
- Take advantage of spacious yards or gardens for outdoor activities and gatherings.
- Make use of fire pits or outdoor fireplaces to cozy up during cool evenings in this destination.
- Access scenic patios or decks that offer stunning views of the surrounding landscape.
- Explore well-maintained walking trails or nature paths nearby for outdoor adventures.
- Utilize outdoor recreational facilities such as sports courts or play areas available at many properties in the region.
Top Attractions Around Oakham
What attractions are nearby?
In this charming region, you can explore a variety of outdoor activities, scenic trails, and local attractions that offer a delightful experience just moments from your vacation rental in Oakham, Massachusetts.
Family Activities
- Oakham's Hiking Trails: Explore scenic trails that offer family-friendly paths suitable for all ages within the region.
- The Local Farm Experience: Visit nearby farms where your family can enjoy hands-on activities and learn about regional agriculture.
- Community Park Activities: Spend quality time at local parks featuring playgrounds, picnic areas, and open spaces perfect for outdoor fun.
- Historic Sites Tour: Discover the area's rich history through visits to well-preserved sites that provide educational opportunities for children and adults alike.
Adult Activities
- Cultural Heritage Tours: Explore the rich history of the region through guided tours that reveal its fascinating past and local landmarks, perfect for history enthusiasts staying in nearby vacation rentals.
- Farmers' Markets and Local Artisanal Shops: Discover fresh produce, handcrafted goods, and unique souvenirs at the area’s farmers' markets, making it a delightful activity to enjoy during your stay.
- Nature Trails and Scenic Walks: Take advantage of the scenic walking trails that wind through the countryside, offering tranquil views and outdoor recreation for visitors in this charming destination.
- Local Dining Experiences: Savor regional cuisine at the town’s cozy restaurants and cafes, providing an authentic taste of the area's culinary delights for guests in nearby accommodations.
Oakham Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature: Take advantage of the many outdoor spaces in the area to enjoy scenic walks, hikes, or wildlife spotting right from your vacation rental.
- Visit Seasonal Events: Plan your stay around local festivals or seasonal celebrations that showcase the regional culture and community spirit.
- Discover Nearby Dining: Savor authentic flavors at nearby eateries or markets, providing a true taste of the area's culinary scene.
- Customize Your Experience: Use local tips and amenities to tailor your activities, ensuring a memorable and personalized stay here.
Transportation Options
- Regional Airport: The nearby regional airport offers convenient flights, making your travel to this part of Massachusetts quick and straightforward.
- Car Rentals: Renting a car is a flexible way to explore the area from your vacation rental, giving you the freedom to visit local attractions at your own pace.
- Public Transit: Local bus services provide an economical and accessible option for getting around here without the need for a private vehicle.
- Taxis and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available in this region, offering quick transportation directly from your vacation rental.
Local Customs Options
- Local Craftsmanship: You can observe the region’s rich tradition of woodworking and handcrafted goods, which are often displayed during community events.
- Seasonal Celebrations: Participating in seasonal festivals and fairs allows you to experience this area's unique approach to celebrating holidays and local traditions.
- Agricultural Practices: The area maintains a strong connection to farming, with visitors often engaging in local farmers' markets that highlight regional produce.
- Community Hospitality: You will find that welcoming attitudes and small-town hospitality are integral parts of life here, especially during neighborhood gatherings and events.
Frequently Asked Questions About Oakham?
1. What are the top vacation rentals in Oakham?
There are a lot of options in Oakham. If you plan on staying in the Oakham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oakham:
- Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
- Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!
- The Inn Crowd Bed and Breakfast
- Leicester Lake Front Home, Come Relax!
- Waterfront Retreat: 2BR with Huge Deck on Lake Lashaway Views in E. Brookfield!
- Hardwick Hygge contemporary retreat with lake views
- Sunnybrook House - 5 bedroom antique home in landscaped wooded grounds.
- Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
- Cozy 3 bedroom home
- Lakefront cabins for family and friend gatherings
2. Which vacation homes in Oakham are best for families?
If you are looking for a family-friendly vacation home in Oakham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oakham:
3. How many Rentbyowner vacation rentals are available in Oakham?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 86 in the Oakham area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Oakham.
4. What is the cancellation policy for vacation rentals in Oakham, Massachusetts?
Cancellation policies vary depending on the listing owner. It is important to review the specific property's cancellation terms detailed in the listing or contact the owner directly for clarification before completing your booking.
5. Are there any additional fees associated with my stay in Oakham vacation rentals?
Additional fees such as cleaning, service charges, or security deposits are typically listed in the property description. To ensure transparency, please review these details on the listing page or reach out to the host for confirmation.
6. How do I confirm the availability of a vacation rental in the area?
Availability calendars are maintained by the property owners and will be updated regularly. You can check real-time availability directly on the listing or contact the host to verify dates before making your reservation.
7. Is it possible to make special requests or customize my stay at vacation rentals here?
Many hosts are open to accommodating special requests such as late check-in, additional amenities, or specific arrangements. Contact the property owner through the messaging system to discuss any personalized needs prior to booking.
8. What should I know about checking in and check-out procedures for vacation rentals in this destination?
Check-in and check-out times are specified in each listing. To ensure a smooth experience, review these details and communicate with the host if you have any questions or need to coordinate your arrival and departure.
Oakham Top Rated Vacation Rentals
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Spa
- Fireplace/Heating
US $199/Night
For 7 Nights US $1,393
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $165/Night
For 7 Nights US $1,153
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $928/Night
For 7 Nights US $6,497
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- View
US $582/Night
For 7 Nights US $4,074
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Pet Friendly
US $126/Night
For 7 Nights US $881
