Vacation rentals in Oakham

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakham

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Wing

4.88 out of 5 average rating, 218 reviews

Quiet Rural Chapel Conversion (Architectural Gem)

Stylish & unique, self- contained historic Chapel conversion overlooking stunning scenery, (Chater Valley) tucked away at the edge of Conservation Village, 5 min drive from R.Water. Private. Sleeps 4 1 king-size & 1 small DBL Kids 8+ welcome Park free outside 2 min walk from King's Arms, Award winning Pub. Quiet & very rural. Grade ii Listed. Modern interior feat. in "Living Etc" & won a local design award Helpful owners next door Completely OPEN PLAN INTERNAL WALLS ONLY AROUND BATHROOM

May 17 – 24

$99 per night
Guest favorite

Condo in Gretton

4.97 out of 5 average rating, 286 reviews

St James’s Cottage - Gretton

An independent, first floor, apartment in a 200yr old cottage. 1 bedroom available as superking bed or twin beds. Separate living room with kitchenette, combination microwave/oven/grill, single zone hob, toaster, kettle and full size fridge. Bathroom with shower. Free WiFi. Private, off road parking outside cottage. Secure garage space available upon request, for locking up bicycles, fishing tackle, golf clubs etc. Set in a lovely, quiet, village with two pubs & coffee shop in walking distance.

Jun 18 – 25

$77 per night
Guest favorite

Cottage in Burley

4.99 out of 5 average rating, 346 reviews

Cosy Country Cottage near Rutland Water

COVID 19 UPDATE: the cottage is still taking bookings and is completely private and deep cleaned between guests. It’s a great place to escape. Gamekeeper Lodge is a characterful, modern and luxurious self catering cottage; and forms a totally private annexe to our Grade 2 listed thatched cottage in the heart of Rutland. The property was designed in 1795 by John Nash, who also designed Buckingham Palace and overlooks the original thatched game larder. Situated only 2 miles from Rutland Water.

Oct 25 – Nov 1

$118 per night

Popular amenities for Oakham vacation rentals

Stay near Oakham's top sights

Oakham Castle19 locals recommend
Captain Noel Newton5 locals recommend
The Admiral Hornblower16 locals recommend
The Lord Nelson17 locals recommend
Lands' End3 locals recommend
Wheatsheaf3 locals recommend

Other great vacation rentals in Oakham

Guest favorite

Guesthouse in Northamptonshire

4.94 out of 5 average rating, 295 reviews

The Old Telephone Exchange

Aug 7 – 14

$90 per night
Guest favorite

Home in Rutland

5.0 out of 5 average rating, 172 reviews

The Haybarn, luxurious Rutland retreat

Sep 13 – 20

$228 per night
Guest favorite

Cottage in Rutland

4.94 out of 5 average rating, 113 reviews

Daphne's cottage

Jan 30 – Feb 6

$95 per night
Guest favorite

Cottage in Wing

4.86 out of 5 average rating, 116 reviews

Stunning Grade II listed thatched cottage

Jul 19 – 26

$343 per night
Guest favorite

Condo in Rutland

5.0 out of 5 average rating, 31 reviews

Mayfield - 1 bedroom annexe flat

Mar 9 – 16

$126 per night
Guest favorite

Condo in Rutland

4.85 out of 5 average rating, 67 reviews

Comfortable, well located, converted apartment.

Jul 3 – 10

$97 per night
Guest favorite

Condo in Braunston

5.0 out of 5 average rating, 10 reviews

Healey House The Annex

Nov 23 – 30

$112 per night
Guest favorite

Apartment in Rutland

4.88 out of 5 average rating, 34 reviews

The Limes - Beautiful Townhouse Apartment, Oakham

Aug 23 – 30

$168 per night
Guest favorite

Condo in Manton

5.0 out of 5 average rating, 23 reviews

Lovely studio annexe in a Rutland Water village

Sep 28 – Oct 5

$86 per night
Guest favorite

Guesthouse in Clipsham

4.89 out of 5 average rating, 47 reviews

Spacious 2 bed barn conversion in Rutland

Jun 6 – 13

$97 per night
Guest favorite

Home in Rutland

5.0 out of 5 average rating, 11 reviews

The Walled Garden HolidayCottage

Aug 2 – 9

$125 per night
Guest favorite

Cottage in Rutland

4.94 out of 5 average rating, 17 reviews

Lovely cottage in Oakham-a calm and relaxing oasis

Apr 8 – 15

$172 per night

Quick stats about vacation rentals in Oakham

Total rentals

50 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

1.2K reviews

Nightly prices starting at

$50 before taxes and fees

Frequently Asked Questions

  • Do house rentals in Oakham have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Oakham. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Oakham?

    Make yourself at home in Oakham by choosing from our most frequently booked neighborhoods. We have over 110 vacation rentals in Braunston-in-Rutland, over 100 vacation rentals in Barleythorpe, and over 100 vacation rentals in Braunston.

  • Do house rentals in Oakham have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Oakham. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Oakham?

    Yes! Work meets play with ease at over 20 vacation rentals in Oakham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Oakham?

    Experience the best of Oakham with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Oakham?

    Four-legged friends are welcome in Oakham. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Oakham have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Oakham. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Oakham?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Rutland
  5. Oakham