Search Vacation Homes in Oakham

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 95 Vacation Homes in Oakham with updated reviews, rates, and availability.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
2 bedrooms, free WiFi

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

9.8 out of 10, Exceptional, (21)
"Love this place. Quiet and has everything you need to feel welcome. Thank you to Eben the host as he is always on top of things"
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Worcester Home on Indian Lake w/ Shared Boat Dock!
Terrace/patio

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (15)
"We enjoyed our stay. It was quiet and relaxing"
Worcester Home on Indian Lake w/ Shared Boat Dock!
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Exterior

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (16)
"Very comfortable VRBO in good location. Quiet, clean without hassles."
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Beautiful two-story home close to downtown worcester 5beds-4bedroom
Fridge, microwave, oven, stovetop

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

8.4 out of 10, Very Good, (8)
"Wonderful Spot for a small group"
The price is AED 668
AED 1,412 total
includes taxes & fees
12 May - 13 May
Beautiful two-story home close to downtown worcester 5beds-4bedroom
Sunnybrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC
Exterior

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
Beautiful Lakefront Home with Private Beach
Lake

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (167)
"We had a great time staying at this property for a post-Christmas family celebration"
Beautiful Lakefront Home with Private Beach
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Fridge, microwave, oven, stovetop

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

2.0 star property
9.8 out of 10, Exceptional, (10)
"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
Spacious Oxford Home w/ Pool - 4 Mi to Lake!
Fridge, microwave, stovetop, dishwasher

Spacious Oxford Home w/ Pool - 4 Mi to Lake!

10.0 out of 10, Exceptional, (4)
"Perfect place as advertised. "
Spacious Oxford Home w/ Pool - 4 Mi to Lake!
Brand new house close to downtown & attractions. Fenced in- Pet/family friendly
Property grounds

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

10.0 out of 10, Exceptional, (8)
"Very comfortable 3 bedroom house. Great location."
Brand new house close to downtown & attractions. Fenced in- Pet/family friendly
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Fridge, microwave, oven, stovetop

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (33)
"The property is very cozy and clean.Excellent location we loved it. Thank you very much."
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Lake House in Sturbridge w/All the Views!
Outdoor spa tub

Lake House in Sturbridge w/All the Views!

9.6 out of 10, Exceptional, (12)
"This was a great visit and we so appreciate the host's consistent communication. The was accurately listed with a killer view of the lake and a hot tub for the ages. Communication is important when renting a house like this, and the host was a 10/10 in coordinating our new year's stay. Thank you so much!"
The price is AED 1,947
AED 3,348 total
includes taxes & fees
9 May - 10 May
Lake House in Sturbridge w/All the Views!
Waterfront New England House on Wickaboag Lake!
TV, table tennis, books, stereo

Waterfront New England House on Wickaboag Lake!

9.8 out of 10, Exceptional, (80)
"Enjoyed this spacious house that easily accommodated our family for my mother's 80th birthday weekend. We were able to cook for everyone, sleep everyone comfortably, and loved hanging out on the deck. Recommend this to families looking to spend some quality time together. "
Waterfront New England House on Wickaboag Lake!
Spacious family friendly 3BR 1st FL apt. Kelly SQ, collages & universities
Fridge, microwave, oven, stovetop

Spacious family friendly 3BR 1st FL apt. Kelly SQ, collages & universities

9.2 out of 10, Wonderful, (28)
"The place was easy to get into. Clean but a little run down. Close to town. We only slept there so it was ok for our group. "
Spacious family friendly 3BR 1st FL apt. Kelly SQ, collages & universities
Sun-Dappled Retreat - Walk to Wickaboag Lake!
Fridge, microwave, stovetop, dishwasher

Sun-Dappled Retreat - Walk to Wickaboag Lake!

10.0 out of 10, Exceptional, (17)
"Excellent property in a convenient location for our family reunion "
Sun-Dappled Retreat - Walk to Wickaboag Lake!
Cozy bedrooms in Shrewsbury warm town and convenient
Interior

Cozy bedrooms in Shrewsbury warm town and convenient

Cozy bedrooms in Shrewsbury warm town and convenient
Indian Lake House
Property grounds

Indian Lake House

8.0 out of 10, Very Good, (1)
"My stay was cozy! Loved the character."
Indian Lake House
Spacious and luxurious 3-bedroom home w/jetted bathtub
Private kitchen

Spacious and luxurious 3-bedroom home w/jetted bathtub

10.0 out of 10, Exceptional, (3)
"Only caveats are the air conditioning is primitive"
Spacious and luxurious 3-bedroom home w/jetted bathtub
Cozy 2-Floor Apartment with Garage Access
Interior

Cozy 2-Floor Apartment with Garage Access

9.6 out of 10, Exceptional, (21)
"The place was great. Very convenient to things. Garage was a big plus. The host was also very responsive and helpful."
Cozy 2-Floor Apartment with Garage Access
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, (86)
"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. "
The price is AED 1,286
AED 2,273 total
includes taxes & fees
31 May - 1 Jun
Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!
Spacious Private Retreat Near Holyoke State Park!
Aerial view

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (7)
"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!
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.
Don't see what you're looking for?
See all available properties in Oakham
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Oakham

Luxury Home, Pool, fireplace
Exterior

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (23)
"The property allowed for my extended family to gather under one roof and spend quality time together in a beautiful and quaint setting. "
Luxury Home, Pool, fireplace
Sunnybrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC
Exterior

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
Interior

Spacious Massachusetts Apartment #2

9.2 out of 10, Wonderful, (19)
"Cute apartment"
Spacious Massachusetts Apartment #2
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.