Oakham Vacation Rentals

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Vacation Rentals in Oakham

Fridge, microwave, oven, stovetop
Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms

Worcester
10.0 out of 10, Exceptional, (5)
"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."
United States
Harmony F.
$446 nightly
The price is $510
Nov 20 - Nov 21
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
Lake
Beautiful Lakefront Home with Private Beach

Beautiful Lakefront Home with Private Beach

Shrewsbury
9.4 out of 10, Exceptional, (181)
"Great location for the family. Grandson enjoyed fishing and family swimming, cookouts and fire pit. "
United States
PeterJanet S.
Beautiful Lakefront Home with Private Beach
Outdoor dining
Leicester Lake Front Home, Come Relax!

Leicester Lake Front Home, Come Relax!

Leicester
10.0 out of 10, Exceptional, (32)
"We had a wonderful 5 days at this lake front home. "
United States
Brandt S.
Leicester Lake Front Home, Come Relax!
Interior
New renovation cozy house in Worcester

New renovation cozy house in Worcester

Worcester
9.8 out of 10, Exceptional, (15)
"A very lovely stay , calm and quiet "
United States
Alex R.
$492 nightly
The price is $563
Dec 5 - Dec 6
Total with taxes and fees
New renovation cozy house in Worcester
Exterior
Dove Cabin up in the Trees

Dove Cabin up in the Trees

Holland
9.8 out of 10, Exceptional, (27)
"Great little getaway - Owners are very friendly and accommodating "
United States
Sharon S.
Dove Cabin up in the Trees
Fridge, microwave, oven, stovetop
Serene 1-bedroom suite on 65 acre horse property

Serene 1-bedroom suite on 65 acre horse property

Belchertown
10.0 out of 10, Exceptional, (22)
"A great jumping off point for the Pioneer Valley and 5 colleges. Brent and Claire were wonderful hosts! Nice and quiet on the property, and it’s a neat experience to have the beautiful horses right outside your window. "
United States
Claire W.
$234 nightly
The price is $247
Nov 24 - Nov 25
Total with taxes and fees
Serene 1-bedroom suite on 65 acre horse property
Exterior
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

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

West Brookfield
10.0 out of 10, Exceptional, (15)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Children's area
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

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

Shrewsbury
9.6 out of 10, Exceptional, (31)
"I stayed at this property for almost a month and thoroughly enjoyed it. It had everything I needed and is conveniently located to Route 9 and I-435. The host was very responsive, which I greatly appreciated. It's nice to know such a comfortable place is available in Shrewsbury."
United States
Patty S.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Exterior
SalsVista 2nd Floor Corner Apt

SalsVista 2nd Floor Corner Apt

Forest Grove
10.0 out of 10, Exceptional, (4)
"We very much enjoyed our weekend stay at this place. The apartment was immaculate and very comfortable."
United States
Anonymous traveler
SalsVista 2nd Floor Corner Apt
Smart TV
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Westminster
10.0 out of 10, Exceptional, (23)
"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "
United States
Michael T.
$471 nightly
The price is $517
Dec 1 - Dec 2
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Exterior
Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2

West Brookfield
9.0 out of 10, Wonderful, (28)
"We used both apartments for time with extended family. Nice to be in the same building."
United States
Tyler K.
$269 nightly
The price is $300
Nov 20 - Nov 21
Total with taxes and fees
Spacious Massachusetts Apartment #2
Property grounds
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

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

Spencer
10.0 out of 10, Exceptional, (199)
"Water front was a perfectly serene escape. House was cute and had everything we needed for a quiet getaway. Would absolutely stay here again. "
United States
Rich L.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Smart TV, fireplace
Home Away from Home!

Home Away from Home!

Worcester
9.4 out of 10, Exceptional, (14)
"The property was nice and accommodating for my family! "
United States
Ykeca M.
$345 nightly
The price is $395
Nov 23 - Nov 24
Total with taxes and fees
Home Away from Home!
Smart TV, books, stereo
Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley

2.0 star property
Belchertown
9.4 out of 10, Exceptional, (20)
"cute little place! host was very responsive"
United States
zane s.
$201 nightly
The price is $212
Nov 20 - Nov 21
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
Property grounds
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

Douglas
10.0 out of 10, Exceptional, (135)
"We had an amazing stay.Very peaceful. It was so nice to be able to have our dog with us. Very enjoyable vacation. "
United States
Ann Marie B.
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
Exterior
Relaxing, Holiday Retreat, Pool, fireplace

Relaxing, Holiday Retreat, Pool, fireplace

Brimfield
10.0 out of 10, Exceptional, (32)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
United States
Danneel A.
Relaxing, Holiday Retreat, Pool, fireplace
Interior
Bungalow 19 by the lake in Brimfield

Bungalow 19 by the lake in Brimfield

2.0 star property
Brimfield
10.0 out of 10, Exceptional, (2)
"Clean, comfortable and great communication with host!"
United States
Elizabeth P.
Bungalow 19 by the lake in Brimfield
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

2.0 star property
Sturbridge
$378 nightly
The price is $422
Nov 20 - Nov 21
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Terrace/patio
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

2.0 star property
Ware
10.0 out of 10, Exceptional, (2)
"We had a great time the place was clean and the owner was nice. I would definitely recommend."
United States
Laura B.
$152 nightly
The price is $161
Nov 20 - Nov 21
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Private kitchen
Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose

Palmer
9.6 out of 10, Exceptional, (8)
"This place is a unique stay, that's for sure! If you are looking for an unforgettable experience, you should come. If you love trains, you should come. However, if you are not that fond of tight spaces or old-fashioned style and your traveling companions are looking for luxury and privacy, you might want to look elsewhere. The bathroom is a big tight (it's a caboose bathroom). But the location is really fun. And the owners are very accommodating! "
United States
Lisa B.
$310 nightly
The price is $328
Nov 23 - Nov 24
Total with taxes and fees
Trainmaster's Inn - Caboose
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

Hilton Garden Inn Worcester

Hilton Garden Inn Worcester

10/10 Excellent
"Great location, polite and helpful staff the room was great, everything worked properly."
Clarice 1-night trip
Posted 2 days ago
Hilton Garden Inn Worcester

Find out more about Oakham

Everything you need to know about Oakham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oakham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $161 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakham rentals

At Expedia, we put the best Oakham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oakham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Oakham?

Yes, we give you a choice of vacation rentals near well known attractions in Oakham, or you can select a more remote option if you're looking for relaxation.

What are some of the best vacation rentals in Oakham?

Spacious 4-bedroom with four and half bathrooms: This vacation home rental near Oakham is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as 1761 Old Mill Gift Shop, or get out into nature at a spot like Rock House Reservation. In the larger area, you’ll find Wachusett Mountain State Reservation and Wachusett Mountain Ski Area.

What’s a vacation rental in Oakham like?

Vacation rentals are private properties where you can stay for a couple of days or more in Oakham. Vacation rentals feature amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a small group gathering.