Vacation rentals in Oakham, MA

31 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Oakham, MA

Cozy Room in the City of Worcester - Oakham, MA

Cozy Room in the City of Worcester

Apartment, Oakham

Cozy Room in the City of Worcester is a apartment in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Cozy Room in the City of Worcester

Cozy Room in the City of Worcester is a apartment in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $557.

From$75/night
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Cozy 2-Floor Apartment with Garage Access - Oakham, MA

Cozy 2-Floor Apartment with Garage Access

Holiday Home, Oakham

Cozy 2-Floor Apartment with Garage Access is a holiday home in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy 2-Floor Apartment with Garage Access

Cozy 2-Floor Apartment with Garage Access is a holiday home in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $957.

From$94/night
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June’s Penthouse: centrally located, downtown, airport, WPI, UMASS - Oakham, MA

June’s Penthouse: centrally located, downtown, airport, WPI, UMASS

Apartment, Oakham

June’s Penthouse: centrally located, downtown, airport, WPI, UMASS is a apartment in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About June’s Penthouse: centrally located, downtown, airport, WPI, UMASS

June’s Penthouse: centrally located, downtown, airport, WPI, UMASS is a apartment in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,211.

From$119/night
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Beautiful Indian Lake Unit, 2nd Floor - Oakham, MA

Beautiful Indian Lake Unit, 2nd Floor

Apartment, Oakham

Beautiful Indian Lake Unit, 2nd Floor is a apartment in Oakham, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Beautiful Indian Lake Unit, 2nd Floor

Beautiful Indian Lake Unit, 2nd Floor is a apartment in Oakham, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,431.

From$141/night
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Best Oakham, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

SalsVista 1st Floor Corner Apt - Oakham, MA

SalsVista 1st Floor Corner Apt

Apartment, Oakham

SalsVista 1st Floor Corner Apt is a apartment in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About SalsVista 1st Floor Corner Apt

SalsVista 1st Floor Corner Apt is a apartment in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,087.

From$214/night
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SalsVista 2nd Floor Corner Apt - Oakham, MA

SalsVista 2nd Floor Corner Apt

Apartment, Oakham

SalsVista 2nd Floor Corner Apt is a apartment in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About SalsVista 2nd Floor Corner Apt

SalsVista 2nd Floor Corner Apt is a apartment in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,146.

From$221/night
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Beautiful Renovated Townhome w/parking - Oakham, MA

Beautiful Renovated Townhome w/parking

Holiday Home, Oakham

Beautiful Renovated Townhome w/parking is a holiday home in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Beautiful Renovated Townhome w/parking

Beautiful Renovated Townhome w/parking is a holiday home in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,950.

From$222/night
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Sun-Dappled Retreat - Walk to Wickaboag Lake! - Oakham, MA

Sun-Dappled Retreat - Walk to Wickaboag Lake!

Holiday Home, Oakham

Sun-Dappled Retreat - Walk to Wickaboag Lake! is a holiday home in Oakham, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Sun-Dappled Retreat - Walk to Wickaboag Lake!

Sun-Dappled Retreat - Walk to Wickaboag Lake! is a holiday home in Oakham, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,503.

From$248/night
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Best Pet-Friendly Vacation Rentals in Oakham, MA

Bring your pet along with stays that welcome four-legged travelers.

Indian Lake House - Oakham, MA

Indian Lake House

Villa, Oakham

Indian Lake House is a villa in Oakham, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Indian Lake House

Indian Lake House is a villa in Oakham, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,724.

From$198/night
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Indian Lake House - Oakham, MA

Indian Lake House

Holiday Home, Oakham

Indian Lake House is a holiday home in Oakham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Indian Lake House

Indian Lake House is a holiday home in Oakham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,877.

From$198/night
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4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni - Oakham, MA

4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni

Apartment, Oakham

4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni is a apartment in Oakham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni

4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni is a apartment in Oakham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,210.

From$233/night
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Sunnybrook House - 5 bedroom antique home in landscaped wooded grounds. - Oakham, MA

Sunnybrook House - 5 bedroom antique home in landscaped wooded grounds.

Holiday Home, Oakham

Sunnybrook House - 5 bedroom antique home in landscaped wooded grounds. is a holiday home in Oakham, with pet-friendly space, parking, and room for a group. This stay gives travelers a…

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About Sunnybrook House - 5 bedroom antique home in landscaped wooded grounds.

Sunnybrook House - 5 bedroom antique home in landscaped wooded grounds. is a holiday home in Oakham, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,444.

From$360/night
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Best Oakham, MA vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Waterfront Retreat: 2BR with Huge Deck on Lake Lashaway Views in E. Brookfield! - Oakham, MA

Waterfront Retreat: 2BR with Huge Deck on Lake Lashaway Views in E. Brookfield!

Apartment, Oakham

Waterfront Retreat: 2BR with Huge Deck on Lake Lashaway Views in E. Brookfield! is a apartment in Oakham, with easy beach access, outdoor space, and kitchen access. This stay gives…

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About Waterfront Retreat: 2BR with Huge Deck on Lake Lashaway Views in E. Brookfield!

Waterfront Retreat: 2BR with Huge Deck on Lake Lashaway Views in E. Brookfield! is a apartment in Oakham, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,285.

From$261/night
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Waterfront 4-bedroom camp-style house in Charlton. Packed with fun for anyone! - Oakham, MA

Waterfront 4-bedroom camp-style house in Charlton. Packed with fun for anyone!

Holiday Home, Oakham

Waterfront 4-bedroom camp-style house in Charlton. Packed with fun for anyone! is a holiday home in Oakham, with pet-friendly space, easy beach access, and parking. This stay gives…

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About Waterfront 4-bedroom camp-style house in Charlton. Packed with fun for anyone!

Waterfront 4-bedroom camp-style house in Charlton. Packed with fun for anyone! is a holiday home in Oakham, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,620.

From$289/night
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Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn - Oakham, MA

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

Cabin, Oakham

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn is a cabin in Oakham, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn is a cabin in Oakham, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,359.

From$360/night
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Warm & Cozy 4BR Near Airport + Winter-Ready Comfort• Fast WiFi - Oakham, MA

Warm & Cozy 4BR Near Airport + Winter-Ready Comfort• Fast WiFi

Holiday Home, Oakham

Warm & Cozy 4BR Near Airport + Winter-Ready Comfort · Fast WiFi is a holiday home in Oakham, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Warm & Cozy 4BR Near Airport + Winter-Ready Comfort• Fast WiFi

Warm & Cozy 4BR Near Airport + Winter-Ready Comfort · Fast WiFi is a holiday home in Oakham, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,904.

From$415/night
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Our Favorite Family-Friendly Vacation Rentals in Oakham, MA

Plan a trip with stays that give families more room to spread out.

Cottage by the Castle – Downtown Spencer - Oakham, MA

Cottage by the Castle – Downtown Spencer

Holiday Home, Oakham

Cottage by the Castle – Downtown Spencer is a holiday home in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer is a holiday home in Oakham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,838.

From$238/night
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Charming 3-bedroom, 1.5 bath house in Worcester - Oakham, MA

Charming 3-bedroom, 1.5 bath house in Worcester

B & B, Oakham

Charming 3-bedroom, 1.5 bath house in Worcester is a b & b in Oakham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Charming 3-bedroom, 1.5 bath house in Worcester

Charming 3-bedroom, 1.5 bath house in Worcester is a b & b in Oakham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,252.

From$253/night
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2 Bedroom Spacious Cottage on pond - Oakham, MA

2 Bedroom Spacious Cottage on pond

Holiday Home, Oakham

2 Bedroom Spacious Cottage on pond is a holiday home in Oakham, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About 2 Bedroom Spacious Cottage on pond

2 Bedroom Spacious Cottage on pond is a holiday home in Oakham, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,787.

From$311/night
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Sun-dappled Retreat - Walk to Wickaboag Lake! - Oakham, MA

Sun-dappled Retreat - Walk to Wickaboag Lake!

Cottage, Oakham

Sun-dappled Retreat - Walk to Wickaboag Lake! is a cottage in Oakham, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Sun-dappled Retreat - Walk to Wickaboag Lake!

Sun-dappled Retreat - Walk to Wickaboag Lake! is a cottage in Oakham, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,861.

From$335/night
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