Holiday Rentals in Oakham

April 2025

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May 2025

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Holiday Rentals in Oakham

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

9.8 out of 10, Exceptional, (21)
"The apartment was very clean and cozy but if you are tall watch out for the low ceilings. Being in an old home it has some wonderful character! The bed was very comfortable as well and has a nice living room with TV. I would highly recommend this place to stay. The host is also very receptive and on top of everything, thank you Ebenezer."
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (182)
"We have used this property for over 4 years now. Just love it and the o"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Home Away from Home!

10.0 out of 10, Exceptional, (2)
"Thank you for our little stay-cation! The property was beautiful and was exactly as expected. Plenty of rooms and bathrooms. My only wish was for more mirrors for us all to do our make up. But we made it work. "
The price is €353
includes taxes & fees
25 May - 26 May
Home Away from Home!

Modern Mid-Century in Fitchburg

10.0 out of 10, Exceptional, (1)
"We had a wonderful time at this property! The house was VERY clean, and beautiful! Very unique decor and style in the home. My husband and myself and our teenage daughter stayed with another couple and their teenage daughter for a Volleyball tournament that was happening at Game on in Fitchburg. We felt right at home after very long days! The house has everything you need for a comfortable stay, and cooking!! We didn’t need anything! The neighborhood is a little under the weather, but please...
Modern Mid-Century in Fitchburg

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (16)
"Very accommodating for our family while visiting our grandson at the university. Slight problem with security to unlock the door. Wrong ID number was provided. House was very clean needs more hooks to hang clothes on bedrooms. I would definitely rent this property again in the future."
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (7)
"It was a quite place to relax. No noise from traffic or people. Short drive to activites to do with family "
Spacious Private Retreat Near Holyoke State Park!

Serene 1-bedroom suite on 65 acre horse property

10.0 out of 10, Exceptional, (12)
"Brent and Claire run a lovely property in every way, especially if you happen to like horses. We will be back!"
Serene 1-bedroom suite on 65 acre horse property

Trainmaster's Inn - Caboose

9.2 out of 10, Wonderful, (5)
"Loved everything about the caboose. Immaculately clean and the attention to detail. The only problem is the beds. They have the old metal springs which one of the most uncomfortable and painful sleeping experiences of my life. Maybe ok for little kids but not a person in their 50’s. We ended up sleeping in the 2 chairs. Area did not have too much but I did love watching the functional trains across the back area. I would give my review 5 stars except for the beds."
The price is €293
includes taxes & fees
27 Apr - 28 Apr
Trainmaster's Inn - Caboose

Apartment in town center #1

8.6 out of 10, Excellent, (14)
"Amazing experience Mattress was like sleeping on a cloud "
Apartment in town center #1

Newly Built Barn Loft in Pioneer Valley

2.0 star property
9.0 out of 10, Wonderful, (7)
"The loft was clean, cozy, and comfortable! Interactions with the host couldn’t have been any better…responsive, polite and professional! Top of list for next stay in Belchertown! Plus near the best bar in Belchertown!"
The price is €171
includes taxes & fees
28 Apr - 29 Apr
Newly Built Barn Loft in Pioneer Valley

Main Street Suite in Sturbridge

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay at the Main St. Suite in Sturbridge. The space was super cute, very clean, and had everything you could need/want and then some. They really thought of it all - and the communication with the hosts was top notch. Thank you for an awesome stay! "
The price is €195
includes taxes & fees
28 Apr - 29 Apr
Main Street Suite in Sturbridge

Sunnybrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We had the most amazing time at Gail’s place. It was even more special, more beautiful, cozy and welcoming than the pictures or descriptions could capture. It is a home, in the very best of ways. Especially in early Spring volatile weather, when it was perfect to be cozy inside, cook, play games, rest. The beds were all comfortable, as was the seating, the space. Kitchen stocked, bathrooms abundant, and everything exceptionally clean. I almost recommended coming when the weather is bad, to take...
Sunnybrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

Spacious Massachusetts Apartment #2

9.2 out of 10, Wonderful, (18)
"Beautiful home"
Spacious Massachusetts Apartment #2

Cozy 2-Floor Apartment with Garage Access

9.6 out of 10, Exceptional, (21)
"The unit is immaculately clean and comfortable. The host is incredibly responsive. I had a sudden and urgent need for her help. She responded to me within a few minutes and all was resolved. The unit is a short distance to WPI. Thank you."
Cozy 2-Floor Apartment with Garage Access

Beautiful & Historic Cottage, Steps to Elm Park

2.5 star property
9.6 out of 10, Exceptional, (5)
"We were visiting Worcester for Holy Cross Family Weekend. Looking for an alternative to booking 2 overpriced hotel rooms, I found this adorable "
Beautiful & Historic Cottage, Steps to Elm Park

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

9.6 out of 10, Exceptional, (20)
"A very relaxing weekend getaway."
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lake House in Sturbridge w/All the Views!

9.6 out of 10, Exceptional, (11)
"The property is beautiful and exactly as pictured. So much to do and such a lovely location on the lake. I wish we had been here in summer, it’s got to be spectacular. Hot tub was well cared for. Snow removal was good. Beds were comfy. Lots of dishes pots and pans. Does not include cooking supplies like oil or seasonings or cooking spray, just fyi. Awesome that we didn’t have to strip beds! Here are some notes that impacted our stay:Not thoroughly cleaned - dirty glass in one of the bedrooms,...
The price is €659
includes taxes & fees
27 Apr - 28 Apr
Lake House in Sturbridge w/All the Views!

LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

2.0 star property
9.0 out of 10, Wonderful, (8)
"House was great and plenty of towels and such. The board games were fabulous. "
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

10.0 out of 10, Exceptional, (8)
"Lovely home, beautifully decorated, safe fenced yard for our furry family. Val responded immediately for something small we needed assistance wuth. Would cone back again."
Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (15)
"Clean, beautiful home"
Worcester Home on Indian Lake w/ Shared Boat Dock!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Oakham you may be interested in

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
8.4 out of 10, Very good, (956)
"I really enjoyed this experience and I hope other people will enjoy this experience."
The price is €209
includes taxes & fees
6 May - 7 May
Great Wolf Lodge Boston / Fitchburg, MA

Wellsworth Hotel

3.0 star property
9.2 out of 10, Wonderful, (1158)
"Midway stopover for a night rest "
The price is €106
includes taxes & fees
11 May - 12 May
Wellsworth Hotel

Comfort Inn Auburn - Worcester

2.5 star property
7.6 out of 10, Good, (946)
"This hotel is in very good location for Boston visitors and the hotel is very clean and maintained high standards of ambience and price very reasonable... "
The price is €109
includes taxes & fees
28 Apr - 29 Apr
Comfort Inn Auburn - Worcester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Are there holiday rentals in Oakham?

Yes, there are holiday rentals close to the most popular sights in Oakham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakham has to offer?

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.: This holiday home rental outside of Oakham has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as EcoTarium, or get out into nature at a spot like Rock House Reservation. In the wider area, you’ll find Hardwick Vineyard and Winery and Wachusett Mountain State Reservation.

What’s a holiday rental in Oakham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakham. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family gatherings.