Oakham Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Oakham Vacation Homes

Spacious Private Retreat Near Holyoke State Park!
Enjoy meals in the kitchen with a dining area featuring a table and chairs.

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (9)
"We stayed for a guys hunting trip and the place was what we needed after a long day"
Spacious Private Retreat Near Holyoke State Park!
Spacious 4-bedroom with four and half bathrooms
Enjoy a view of the surrounding area from the large window in this kitchen, featuring a double sink and sleek appliances.

Spacious 4-bedroom with four and half bathrooms

10.0 out of 10, Exceptional, (1)
"We had room for each of the adults, which included adult children. At these ages they no longer want to share a bed or bathroom with anyone. Perfect that we could come together, but have our own separate spaces. Very clean and comfortable with everything you need."
The price is CA $378
CA $702 total
includes taxes & fees
Aug 11 - Aug 12
Spacious 4-bedroom with four and half bathrooms
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Situated in a wooded area, this single-story house features a front porch and a stone retaining wall.

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (20)
"Matressess were outdated but otherwise great!"
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Beautiful Renovated Townhome w/parking
Step out onto the covered porch, flanked by a railing and street view, and enjoy the serene atmosphere.

Beautiful Renovated Townhome w/parking

9.4 out of 10, Exceptional, (16)
"Great communication, assistance with maintenance, and receptive to feedback. Would stay again . "
Beautiful Renovated Townhome w/parking
3 Bed / 1.5 Bath Townhome
Enjoy meals in the well-lit kitchen with stainless steel appliances, white cabinetry, and a dining area.

3 Bed / 1.5 Bath Townhome

9.2 out of 10, Wonderful, (16)
"You will hear a little road noice but other then that it was perfect! Extremely clean and a great location. Highly recommend "
3 Bed / 1.5 Bath Townhome
Beautiful two-story home close to downtown worcester 5beds-4bedroom
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and refrigerator.

Beautiful two-story home close to downtown worcester 5beds-4bedroom

9.0 out of 10, Wonderful, (13)
"Nice place."
The price is CA $272
CA $570 total
includes taxes & fees
Aug 21 - Aug 22
Beautiful two-story home close to downtown worcester 5beds-4bedroom
New renovation cozy house in Worcester
Decorative table features a variety of plants, a globe, and a golden sculpture.

New renovation cozy house in Worcester

9.8 out of 10, Exceptional, (11)
"This was a great spot for myself and my coaches when we had to travel to the area for a cheerleading competition."
New renovation cozy house in Worcester
Brand new 3 bedroom house in welcoming Worcester with WiFi and AC
Enjoy cooking in this well-equipped kitchen with stainless steel appliances and a central island.

Brand new 3 bedroom house in welcoming Worcester with WiFi and AC

9.0 out of 10, Wonderful, (2)
"House was new, bright, and clean. "
Brand new 3 bedroom house in welcoming Worcester with WiFi and AC
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!
Relax on the deck overlooking the serene lake, surrounded by lush greenery.

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!
Modern 4BR Escape in Worcester AC • Huge Yard • Fast WiFi
Microwave, oven, stovetop, dishwasher

Modern 4BR Escape in Worcester AC • Huge Yard • Fast WiFi

The price is CA $216
CA $751 total
includes taxes & fees
Aug 12 - Aug 13
Modern 4BR Escape in Worcester AC • Huge Yard • Fast WiFi
Cozy bedrooms in Shrewsbury warm town and convenient
Relax in a serene garden setting surrounded by blooming trees and a well-maintained path.

Cozy bedrooms in Shrewsbury warm town and convenient

Cozy bedrooms in Shrewsbury warm town and convenient
Beautiful Lakefront Home with Private Beach
Surrounded by vibrant autumn colors, this serene lakeside setting offers a peaceful escape.

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (173)
"Beautiful house and grounds! Very private with lots of room along with homey touches. Kids loved the toy cabinet and the pool table. Easy access to Boston. We thoroughly enjoyed our Easter weekend there! "
Beautiful Lakefront Home with Private Beach
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Hammock suspended between trees, offering a serene spot to relax by the water.

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (190)
"This was our third time staying, and definately won’t be our last!"
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!
Snow and ski sports

Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

9.8 out of 10, Exceptional, (87)
"My family stayed here while in town for a family wedding. The house was very spacious and well stocked. Location was convenient for our events in Westminster. "
Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!
Leicester Lake Front Home, Come Relax!
Enjoy al fresco dining on the deck overlooking the water, where a barbecue grill and comfortable seating await.

Leicester Lake Front Home, Come Relax!

10.0 out of 10, Exceptional, (26)
"Great family time and comfortable house to spend time with family during a visit to see our daughter at Holy Cross! "
Leicester Lake Front Home, Come Relax!
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Relax on the covered porch, surrounded by a peaceful lawn and mature trees.

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

9.8 out of 10, Exceptional, (10)
"Property is in excellent condition and well appointed. We enjoyed our stay."
The price is CA $445
CA $826 total
includes taxes & fees
Sep 9 - Sep 10
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Home Away from Home!
Relax in this inviting living area with a high ceiling, ceiling fan, and comfortable seating for two.

Home Away from Home!

9.2 out of 10, Wonderful, (11)
"Lots of bedrooms with a great family gathering space. Quiet neighborhood. Would stay again at this property. Nicely decorated. "
The price is CA $256
CA $543 total
includes taxes & fees
Aug 11 - Aug 12
Home Away from Home!
Spacious and luxurious 3-bedroom home w/jetted bathtub
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and dark cabinetry.

Spacious and luxurious 3-bedroom home w/jetted bathtub

9.2 out of 10, Wonderful, (5)
"Only caveats are the air conditioning is primitive"
Spacious and luxurious 3-bedroom home w/jetted bathtub
Lakefront Cottage 2 Mi to Palladium in Worcester!
Enjoy cooking in this well-equipped kitchen with a central island, dishwasher, and ample counter space.

Lakefront Cottage 2 Mi to Palladium in Worcester!

10.0 out of 10, Exceptional, (3)
"The space was clean and welcoming, very comfortable. The location was excellent for my son's week at WPI. "
Lakefront Cottage 2 Mi to Palladium in Worcester!
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and coffee maker.

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (16)
"Our stay at this property was great. Very clean and spacious. Area was very accessible to main roads. Our hosts were very responsive from booking through to the end of our stay. Will look to stay next time we visit Worcester "
Spacious 4-bedroom house in charming Worcester with AC, WiFi
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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Top Oakham Hotel Reviews

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Wonderful hotel!! Historic and beautiful!! Friendly staff!! Excellent on-site restaurant! Definitely will be staying there in the future!!"
Anonymous traveller 1-night trip
Posted 2 days ago
Wellsworth Hotel