Vacation rentals in Oxford

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Top-rated vacation rentals in Oxford

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

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Guest favorite
A charming two-story house is nestled by the water, featuring a wraparound deck adorned with seating. The landscaped yard includes rocky pathways and a small gathering area with Adirondack chairs, inviting moments of relaxation by the water's edge.
Home in Sturbridge
4.94 out of 5 average rating, 324 reviews

Lake Front Home Sleeps 6-8 on a private Peninsula!

Stunning year-round waterfront home on its own private peninsula—sleeps 6–8 with 3BR/2BA, a spacious living room with sliders to a wraparound deck, and a heated sun porch offering panoramic lake views. Nearly every window overlooks the water. Outside, enjoy a private dock, new stone patio & firepit, small beach area, kayaks, canoe, and rowboat. Perfect for families, couples, or a friends’ getaway. See walkthrough videos at on YouTube @CedarLakeCottage Summer: 4-night min | Holidays: 3-night min

Superhost
Cottage in Dudley
4.85 out of 5 average rating, 54 reviews

Cozy, 3BR lake-side retreat and outdoor oasis

Escape to our peaceful private lakefront cottage in Dudley, MA, your perfect year-round retreat! Recently updated 3-bed, 2-bath home on beautiful Pierpoint Meadow Lake offers swimming, fishing, kayaking, vibrant fall colors, and winter ice skating. Inside, enjoy air conditioning, cozy fireplace, dishwasher, washer/dryer, and new TVs. Outside, relax on the new multi-level deck with stunning lake views, gather by the fire pit, or step onto your private dock and sandy beach to make lasting memories

Top guest favorite
A spacious deck overlooks a calm lake, reflecting the surrounding trees in warm autumn colors. Several wooden chairs and a circular table are arranged comfortably, with an umbrella providing shade. The setting offers a serene atmosphere, ideal for relaxation or enjoying nature.
Home in Oakham
4.99 out of 5 average rating, 192 reviews

Lovely & Peaceful Waterfront Vacation Retreat

Come enjoy this unique & beautiful retreat home, set on 50 acres of wooded land, with a breath-taking view over a 2 mile long, 190-acre body of water, & no houses in sight! Wonderful in any season. Peaceful, healing haven, & great get-away spot for a romantic weekend or family vacation. Perfect for swimming, boating, fishing, hiking, & cross-country skiing--or just relaxing in a hammock, on the deck, or in a bedroom overlooking the water. Youtube Video: Fred's Place, James Crowther

Top guest favorite
A spacious living area highlights a comfortable gray sofa, complemented by a wooden coffee table at the center. A large television is mounted on the wall, and natural light enters through multiple windows adorned with white trim.
Apartment in Worcester
4.96 out of 5 average rating, 114 reviews

Centrally Located Apartment in Worcester

This first-floor unit in a charming 1910 duplex offers modern comfort and unbeatable convenience. Located within half a mile of Worcester State University and a grocery store, and within walking distance of restaurants and shops, it’s perfect for any lifestyle. The updated space features lightning-fast 1 Gbps WiFi, two workspaces, off-street parking for one car, and plenty of on-street parking. Ideal for both work and relaxation, this home is fully equipped for a comfortable stay.

Guest favorite
A spacious living area is presented with a comfortable sectional sofa and a coffee table. A brick fireplace serves as a central feature, while a wall-mounted television is visible. Light streams in through nearby windows, enhancing the warm ambiance of the room.
Home in Worcester
4.94 out of 5 average rating, 118 reviews

LuxuryHaven: Cosy Palace

Spacious and newly renovated private house in a central but unique location next to College of the Holy Cross, very close to many restaurants, shopping mall/plaza, DCU center, Clark University, WPI and UMassMed. This newly renovated and private house is decorated to offer the comfort of home away from home with newly furnished kitchen, bedrooms, dinning, living room and office/gym space. The whole group will enjoy easy access to everything from this centrally located place.

Top guest favorite
A single-story farmhouse features a covered front porch adorned with hanging plants. A well-maintained lawn surrounds the home, complemented by landscaped bushes. An American flag is displayed, and tall trees line the background, providing a natural setting.
Guest suite in Thompson
4.98 out of 5 average rating, 197 reviews

Meadowside: Perfect Location w/ Endless Recreation

Perfect location, great value, & tons of privacy! Come stay at Meadowside! You'll be in a beautifully appointed and completely private 620 sq ft in-law suite. We're a quarter mile away from Webster Lake and an easy drive to all area attractions! Bring your boat, as we have plenty of room for your trailer in our parking lot-sized driveway! A king bed in the master, 1.5 baths, kitchen, laundry, front farmer's porch, and garden dining! You name it, it's here at Meadowside!

Guest favorite
Home in Woodstock
4.97 out of 5 average rating, 33 reviews

The McClellan Mansion

Resting on a sprawling estate in picturesque Woodstock, CT, this fully restored historic home blends timeless architecture with modern luxury, it offers grand spaces, cozy corners, a chef’s kitchen, spa baths, and manicured grounds. Pair with our poolside cottage for extra space and pool access. This Woodstock estate is more than a stay—it’s a destination. Pool is only included by booking the additional listing “Poolside Cottage”.

Guest favorite
A spacious bedroom features a large bed adorned with a patterned green and white quilt. Natural light floods the room through multiple windows, highlighting a small desk and ergonomic chair. Soft lighting is provided by sconces on the walls.
Guesthouse in Worcester
4.82 out of 5 average rating, 117 reviews

Quiet Oasis In The City

Forget your worries in this spacious and serene space. We are right in the city but you'll feel miles away. This two level guest home is surrounded by nature and very relaxing. Two bedrooms and two baths. Two king sized beds. One full bath with oversized tub downstairs. Upstairs bath with standing shower. Full kitchen and coffee and tea. Hot tub is included with BNB. Pool is a separate rental. Message for details.

Guest favorite
A close-up of a wooden patio table is shown, featuring a central hole for an umbrella. In the background, the tranquil lake reflects the overcast sky, flanked by trees and developed areas along the shore.
Home in Webster
4.93 out of 5 average rating, 40 reviews

Webster Lake - One Home / Two Apartments

Imagine the possibilities! Perfect for large families, multiple groups, or those simply craving extra space and privacy, this unique home offers the best of both worlds: two separate, fully equipped apartments under one roof! Whether you're planning a multi-generational getaway, a reunion with friends, or need separate quarters for your group, this property provides unparalleled flexibility.

Superhost
A living room area features a comfortable black sofa with red accents and a patterned armchair. A coffee table occupies the center, surrounded by a decorative area rug. Natural light enters through windows adorned with sheer curtains, while a potted plant adds a touch of greenery.
Apartment in Dudley
4.82 out of 5 average rating, 573 reviews

웃❤️유 PRIVATE STUDIO - SAFE GORGEOUS HIDEOUT

Excellent for couples; voyagers & professionals. Ideal for short or long terms stays, everything is incld. Cozy, bright and small very comfy bedroom, if business travel or just visiting the area, Kitchen, living room and Laptop Desk. Self-Check-In, Wi-Fi, free & safe on-street Parking, Lock on Door, A/C, we are in a busy street during the day but really safe

Top guest favorite
Home in Shrewsbury
4.98 out of 5 average rating, 44 reviews

Historical New England retreat

Relax and recharge at this beautiful antique colonial home. Built in 1749 and steeped in local history, this home offers the perfect blend of classic architectural details and modern comforts. Wake to fresh eggs from our chickens, pick seasonal fruit from espaliered trees, and unwind in thoughtfully designed spaces that feel like home.

Superhost
A pathway leads down to the tranquil waters of Lake Quinsig, surrounded by lush greenery. Soft clouds drift across a bright blue sky, reflecting light on the calm surface of the lake. Boat docks are visible, inviting leisurely activities.
Home in Worcester
4.9 out of 5 average rating, 135 reviews

Million-Dollar View - Great Location/Sleeps 9

Escape to a million-dollar view at our charming 3-bdrm lake house, nestled on the shores of Lake Quinsig. Despite the serene surroundings, you are just a short drive from downtown Worcester, where you can explore local shops and restaurants or maybe enjoy a concert. Ideal for families, friends or couples seeking a getaway.

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